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The title compound, C
24H
21N
3O
6·2CH
2Cl
2, crystallizes with two independent molecules in the asymmetric unit, each with a different conformation. In the crystal structure, molecules form two-dimensional sheets in the
ab plane due to a combination of O—H
O and N—H
O hydrogen bonds. Only edge-to-face stacking interactions are observed between fluorenyl aromatic groups of adjacent sheets. Solvent molecules are located within the intermolecular voids along the
b axis and fill the spaces between carbamate linkages or lie between the fluorenyl aromatic groups.
Supporting information
CCDC reference: 618981
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.061
- wR factor = 0.112
- Data-to-parameter ratio = 22.2
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor .... 5.45
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C50
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C60
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 20.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 10
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4
C H2 Cl2
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 33.00
From the CIF: _reflns_number_total 15906
Count of symmetry unique reflns 11432
Completeness (_total/calc) 139.14%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 4474
Fraction of Friedel pairs measured 0.391
Are heavy atom types Z>Si present yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2A = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2B = . S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12A = . R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12B = . S
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
5 ALERT level G = General alerts; check
5 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
6 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
| Author Response: Stefanowicz Piotr, resoinsible for idea of compound synthesis,
Jaremko \/Lukasz, responsible for manuscript preparation, Jaremko Mariusz,
responsible for manuscript preparation, Staszewska Anna, responsible
for performing the synthesis, Szewczuk Zbigniew, main author of
the idea for project concerning the title compound, Bryndal Iwona,;
responsible for structure solution, X-ray measurements
and manuscript preparation, Lis Tadeusz, responsile for structure solution
and X-ray measurements
|
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
(2
S)-3-(4-Amino-3-nitrophenyl)-2-(9
H-fluoren-9-ylmethoxycarbonylamino)propanoic acid dichloromethane disolvate
top
Crystal data top
C24H21N3O6·2CH2Cl2 | F(000) = 1272 |
Mr = 617.29 | Dx = 1.415 Mg m−3 |
Monoclinic, P21 | Melting point: 438 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 12.362 (3) Å | Cell parameters from 12599 reflections |
b = 10.489 (3) Å | θ = 3.3–30.0° |
c = 22.958 (4) Å | µ = 0.45 mm−1 |
β = 103.17 (3)° | T = 100 K |
V = 2898.6 (12) Å3 | Block, yellow |
Z = 4 | 0.25 × 0.2 × 0.15 mm |
Data collection top
Oxford Diffraction KM-4-CCD diffractometer | 15906 independent reflections |
Radiation source: fine-focus sealed tube | 9639 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 33.0°, θmin = 3.3° |
Absorption correction: numerical (CrysAlisRED; Oxford Diffraction, 2003) | h = −18→18 |
Tmin = 0.913, Tmax = 0.947 | k = −16→12 |
44865 measured reflections | l = −35→34 |
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)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0457P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
15906 reflections | Δρmax = 0.51 e Å−3 |
715 parameters | Δρmin = −0.54 e Å−3 |
7 restraints | Absolute structure: Flack (1983), with 4474 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.12 (4) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1A | 0.50747 (15) | 0.68992 (17) | 0.06903 (8) | 0.0200 (4) | |
O2A | 0.35497 (15) | 0.61680 (18) | 0.00490 (8) | 0.0224 (4) | |
H2OA | 0.3509 | 0.6920 | −0.0080 | 0.027* | |
O3A | 0.45934 (17) | −0.04129 (18) | 0.26065 (8) | 0.0235 (4) | |
O4A | 0.45313 (17) | 0.15834 (18) | 0.28255 (8) | 0.0246 (4) | |
O5A | 0.65010 (14) | 0.34547 (17) | 0.04272 (7) | 0.0149 (4) | |
O6A | 0.73120 (14) | 0.34610 (17) | 0.14191 (8) | 0.0160 (4) | |
N1A | 0.56961 (16) | 0.4457 (2) | 0.10964 (9) | 0.0130 (4) | |
H1A | 0.5804 | 0.4796 | 0.1456 | 0.016* | |
N2A | 0.44883 (18) | 0.0732 (2) | 0.24476 (9) | 0.0164 (5) | |
N3A | 0.4600 (2) | −0.1133 (2) | 0.15041 (10) | 0.0223 (5) | |
H3A1 | 0.4732 | −0.1421 | 0.1874 | 0.027* | |
H3A2 | 0.4623 | −0.1656 | 0.1207 | 0.027* | |
C1A | 0.4458 (2) | 0.6038 (2) | 0.04807 (11) | 0.0155 (5) | |
C2A | 0.4642 (2) | 0.4643 (2) | 0.06677 (11) | 0.0130 (5) | |
H2A | 0.4671 | 0.4141 | 0.0301 | 0.016* | |
C3A | 0.3670 (2) | 0.4117 (2) | 0.09152 (12) | 0.0162 (5) | |
H311 | 0.3599 | 0.4615 | 0.1271 | 0.019* | |
H312 | 0.2967 | 0.4200 | 0.0608 | 0.019* | |
C4A | 0.3876 (2) | 0.2729 (2) | 0.10849 (11) | 0.0137 (5) | |
C5A | 0.4063 (2) | 0.2338 (2) | 0.16716 (11) | 0.0139 (5) | |
H5A | 0.4034 | 0.2942 | 0.1976 | 0.017* | |
C6A | 0.4298 (2) | 0.1043 (2) | 0.18268 (11) | 0.0150 (5) | |
C7A | 0.4362 (2) | 0.0104 (2) | 0.13930 (11) | 0.0150 (5) | |
C8A | 0.4154 (2) | 0.0540 (2) | 0.07891 (11) | 0.0167 (5) | |
H8A | 0.4180 | −0.0053 | 0.0480 | 0.020* | |
C9A | 0.3916 (2) | 0.1801 (3) | 0.06428 (11) | 0.0161 (5) | |
H9A | 0.3776 | 0.2053 | 0.0235 | 0.019* | |
C10A | 0.6498 (2) | 0.3772 (2) | 0.09447 (11) | 0.0124 (5) | |
C11A | 0.8200 (2) | 0.2692 (3) | 0.12739 (11) | 0.0178 (5) | |
H1A1 | 0.8594 | 0.3188 | 0.1019 | 0.021* | |
H1A2 | 0.7884 | 0.1919 | 0.1052 | 0.021* | |
C12A | 0.9003 (2) | 0.2318 (3) | 0.18500 (11) | 0.0152 (5) | |
H12A | 0.9326 | 0.3097 | 0.2075 | 0.018* | |
C13A | 0.9924 (2) | 0.1501 (3) | 0.17000 (11) | 0.0166 (5) | |
C14A | 1.0661 (2) | 0.1811 (3) | 0.13510 (12) | 0.0208 (6) | |
H14A | 1.0634 | 0.2624 | 0.1166 | 0.025* | |
C15A | 1.1447 (2) | 0.0902 (3) | 0.12764 (12) | 0.0241 (6) | |
H15A | 1.1952 | 0.1088 | 0.1032 | 0.029* | |
C16A | 1.1489 (2) | −0.0278 (3) | 0.15605 (13) | 0.0234 (6) | |
H16A | 1.2040 | −0.0879 | 0.1516 | 0.028* | |
C17A | 1.0741 (2) | −0.0594 (3) | 0.19077 (12) | 0.0212 (6) | |
H17A | 1.0766 | −0.1406 | 0.2094 | 0.025* | |
C18A | 0.9954 (2) | 0.0310 (3) | 0.19758 (11) | 0.0155 (5) | |
C19A | 0.9085 (2) | 0.0271 (3) | 0.23189 (11) | 0.0170 (5) | |
C20A | 0.8795 (2) | −0.0685 (3) | 0.26794 (12) | 0.0208 (6) | |
H20A | 0.9177 | −0.1478 | 0.2727 | 0.025* | |
C21A | 0.7940 (2) | −0.0459 (3) | 0.29679 (13) | 0.0275 (7) | |
H21A | 0.7736 | −0.1101 | 0.3215 | 0.033* | |
C22A | 0.7381 (2) | 0.0704 (3) | 0.28969 (13) | 0.0284 (7) | |
H22A | 0.6798 | 0.0846 | 0.3096 | 0.034* | |
C23A | 0.7663 (2) | 0.1663 (3) | 0.25377 (12) | 0.0233 (6) | |
H23A | 0.7275 | 0.2452 | 0.2487 | 0.028* | |
C24A | 0.8528 (2) | 0.1438 (3) | 0.22551 (11) | 0.0162 (5) | |
O1B | 0.51099 (16) | 1.18527 (18) | 0.43616 (8) | 0.0220 (4) | |
O2B | 0.64840 (16) | 1.10912 (18) | 0.50908 (8) | 0.0223 (4) | |
H2OB | 0.6516 | 1.1847 | 0.5215 | 0.027* | |
O3B | 0.54907 (17) | 0.46849 (18) | 0.24280 (8) | 0.0241 (4) | |
O4B | 0.56097 (18) | 0.67111 (19) | 0.22676 (8) | 0.0275 (5) | |
O5B | 0.33648 (14) | 0.85061 (17) | 0.45331 (8) | 0.0169 (4) | |
O6B | 0.26709 (14) | 0.89983 (18) | 0.35571 (8) | 0.0181 (4) | |
N1B | 0.44199 (18) | 0.9478 (2) | 0.39692 (9) | 0.0163 (4) | |
H1B | 0.4428 | 0.9775 | 0.3612 | 0.020* | |
N2B | 0.56075 (18) | 0.5810 (2) | 0.26140 (9) | 0.0169 (5) | |
N3B | 0.5576 (2) | 0.3807 (2) | 0.35106 (10) | 0.0224 (5) | |
H3B1 | 0.5605 | 0.3232 | 0.3793 | 0.027* | |
H3B2 | 0.5415 | 0.3576 | 0.3132 | 0.027* | |
C1B | 0.5640 (2) | 1.0970 (2) | 0.46229 (10) | 0.0151 (5) | |
C2B | 0.5423 (2) | 0.9572 (3) | 0.44401 (11) | 0.0145 (5) | |
H2B | 0.5310 | 0.9081 | 0.4795 | 0.017* | |
C3B | 0.6424 (2) | 0.9004 (3) | 0.42367 (11) | 0.0169 (5) | |
H321 | 0.6576 | 0.9523 | 0.3904 | 0.020* | |
H322 | 0.7088 | 0.9044 | 0.4572 | 0.020* | |
C4B | 0.6226 (2) | 0.7635 (2) | 0.40322 (11) | 0.0162 (5) | |
C5B | 0.5982 (2) | 0.7321 (2) | 0.34366 (11) | 0.0148 (5) | |
H5B | 0.5948 | 0.7976 | 0.3147 | 0.018* | |
C6B | 0.5781 (2) | 0.6051 (2) | 0.32447 (11) | 0.0145 (5) | |
C7B | 0.5779 (2) | 0.5043 (2) | 0.36579 (11) | 0.0164 (5) | |
C8B | 0.6038 (2) | 0.5391 (3) | 0.42715 (12) | 0.0192 (6) | |
H8B | 0.6062 | 0.4750 | 0.4567 | 0.023* | |
C9B | 0.6255 (2) | 0.6641 (3) | 0.44491 (11) | 0.0182 (5) | |
H9B | 0.6429 | 0.6836 | 0.4864 | 0.022* | |
C10B | 0.3482 (2) | 0.8955 (2) | 0.40585 (10) | 0.0140 (5) | |
C11B | 0.1626 (2) | 0.8393 (3) | 0.35876 (13) | 0.0204 (6) | |
H1B1 | 0.1014 | 0.8780 | 0.3285 | 0.025* | |
H1B2 | 0.1475 | 0.8543 | 0.3987 | 0.025* | |
C12B | 0.1662 (2) | 0.6956 (3) | 0.34746 (12) | 0.0185 (5) | |
H12B | 0.2249 | 0.6542 | 0.3790 | 0.022* | |
C13B | 0.0529 (2) | 0.6372 (3) | 0.34641 (12) | 0.0209 (6) | |
C14B | −0.0051 (2) | 0.6335 (3) | 0.39183 (14) | 0.0294 (7) | |
H14B | 0.0254 | 0.6703 | 0.4298 | 0.035* | |
C15B | −0.1092 (3) | 0.5745 (3) | 0.38028 (16) | 0.0349 (8) | |
H15B | −0.1494 | 0.5696 | 0.4109 | 0.042* | |
C16B | −0.1542 (3) | 0.5229 (3) | 0.32400 (16) | 0.0342 (8) | |
H16B | −0.2248 | 0.4824 | 0.3169 | 0.041* | |
C17B | −0.0981 (2) | 0.5294 (3) | 0.27807 (15) | 0.0272 (7) | |
H17B | −0.1308 | 0.4970 | 0.2394 | 0.033* | |
C18B | 0.0073 (2) | 0.5848 (3) | 0.29007 (13) | 0.0209 (6) | |
C19B | 0.0874 (2) | 0.5996 (3) | 0.25230 (12) | 0.0215 (6) | |
C20B | 0.0826 (2) | 0.5625 (3) | 0.19331 (14) | 0.0287 (7) | |
H20B | 0.0188 | 0.5203 | 0.1706 | 0.034* | |
C21B | 0.1724 (3) | 0.5881 (3) | 0.16831 (14) | 0.0313 (7) | |
H21B | 0.1700 | 0.5630 | 0.1283 | 0.038* | |
C22B | 0.2658 (2) | 0.6502 (3) | 0.20127 (14) | 0.0283 (7) | |
H22B | 0.3261 | 0.6677 | 0.1832 | 0.034* | |
C23B | 0.2728 (2) | 0.6872 (3) | 0.26036 (12) | 0.0224 (6) | |
H23B | 0.3374 | 0.7283 | 0.2829 | 0.027* | |
C24B | 0.1823 (2) | 0.6623 (2) | 0.28553 (12) | 0.0181 (5) | |
Cl1 | −0.26953 (8) | 0.89283 (8) | 0.08922 (4) | 0.0445 (2) | |
Cl2 | −0.19003 (7) | 0.63040 (8) | 0.08664 (4) | 0.0424 (2) | |
C30 | −0.2405 (3) | 0.7484 (3) | 0.12973 (14) | 0.0405 (9) | |
H301 | −0.3090 | 0.7169 | 0.1404 | 0.049* | |
H302 | −0.1843 | 0.7640 | 0.1673 | 0.049* | |
Cl3 | 0.7247 (2) | 0.8811 (3) | 0.59695 (16) | 0.0396 (6) | 0.764 (6) |
Cl4 | 0.8450 (2) | 0.7309 (3) | 0.70065 (11) | 0.0796 (9) | 0.764 (6) |
C40 | 0.7272 (5) | 0.7495 (6) | 0.6435 (2) | 0.058 (2) | 0.764 (6) |
H401 | 0.6620 | 0.7549 | 0.6617 | 0.070* | 0.764 (6) |
H402 | 0.7182 | 0.6718 | 0.6184 | 0.070* | 0.764 (6) |
Cl31 | 0.7556 (8) | 0.8714 (13) | 0.5978 (6) | 0.0396 (6) | 0.236 (6) |
Cl41 | 0.8038 (7) | 0.7773 (9) | 0.7161 (4) | 0.0796 (9) | 0.236 (6) |
C401 | 0.751 (3) | 0.7373 (18) | 0.6417 (4) | 0.058 (2) | 0.236 (6) |
H411 | 0.6733 | 0.7072 | 0.6360 | 0.070* | 0.236 (6) |
H412 | 0.7956 | 0.6678 | 0.6298 | 0.070* | 0.236 (6) |
Cl5 | 0.14199 (8) | 0.79174 (14) | 0.02583 (4) | 0.0656 (4) | |
Cl6 | −0.04682 (11) | 0.96014 (12) | −0.01272 (6) | 0.0818 (4) | |
C50 | 0.0034 (3) | 0.8244 (4) | 0.02774 (15) | 0.0412 (9) | |
H501 | −0.0436 | 0.7506 | 0.0111 | 0.049* | |
H502 | −0.0018 | 0.8357 | 0.0698 | 0.049* | |
Cl7 | 0.15154 (9) | 0.74663 (16) | 0.56067 (6) | 0.0796 (4) | |
Cl8 | −0.06225 (12) | 0.61957 (15) | 0.55271 (6) | 0.0851 (4) | |
C60 | 0.0379 (3) | 0.7227 (5) | 0.59415 (19) | 0.0604 (12) | |
H601 | 0.0655 | 0.6870 | 0.6347 | 0.073* | |
H602 | 0.0029 | 0.8060 | 0.5984 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0245 (10) | 0.0156 (9) | 0.0178 (9) | −0.0003 (8) | 0.0003 (8) | 0.0001 (8) |
O2A | 0.0232 (10) | 0.0140 (9) | 0.0248 (10) | −0.0017 (8) | −0.0057 (8) | 0.0101 (8) |
O3A | 0.0381 (12) | 0.0138 (9) | 0.0189 (9) | 0.0023 (9) | 0.0071 (9) | 0.0073 (8) |
O4A | 0.0414 (12) | 0.0207 (10) | 0.0114 (9) | −0.0010 (9) | 0.0049 (8) | −0.0032 (8) |
O5A | 0.0177 (9) | 0.0131 (9) | 0.0131 (8) | 0.0035 (7) | 0.0016 (7) | −0.0032 (7) |
O6A | 0.0165 (9) | 0.0167 (9) | 0.0137 (8) | 0.0075 (7) | 0.0010 (7) | −0.0005 (7) |
N1A | 0.0159 (10) | 0.0122 (10) | 0.0091 (9) | 0.0009 (8) | −0.0011 (8) | −0.0011 (8) |
N2A | 0.0210 (11) | 0.0146 (11) | 0.0138 (10) | −0.0008 (9) | 0.0041 (9) | 0.0038 (9) |
N3A | 0.0371 (14) | 0.0112 (11) | 0.0199 (11) | 0.0046 (10) | 0.0092 (10) | 0.0016 (9) |
C1A | 0.0232 (13) | 0.0110 (12) | 0.0141 (12) | 0.0031 (10) | 0.0081 (10) | 0.0046 (10) |
C2A | 0.0157 (12) | 0.0122 (12) | 0.0101 (11) | 0.0020 (10) | 0.0006 (9) | 0.0011 (10) |
C3A | 0.0163 (12) | 0.0135 (12) | 0.0195 (12) | 0.0021 (10) | 0.0057 (10) | 0.0025 (10) |
C4A | 0.0125 (12) | 0.0135 (12) | 0.0160 (12) | −0.0017 (10) | 0.0052 (10) | −0.0001 (10) |
C5A | 0.0164 (12) | 0.0104 (11) | 0.0154 (12) | −0.0005 (10) | 0.0044 (10) | −0.0015 (10) |
C6A | 0.0183 (13) | 0.0142 (12) | 0.0127 (11) | −0.0008 (10) | 0.0041 (10) | 0.0025 (10) |
C7A | 0.0187 (13) | 0.0117 (12) | 0.0168 (12) | 0.0004 (10) | 0.0086 (10) | −0.0006 (10) |
C8A | 0.0214 (13) | 0.0166 (13) | 0.0129 (12) | −0.0004 (11) | 0.0058 (10) | −0.0025 (10) |
C9A | 0.0190 (13) | 0.0192 (13) | 0.0106 (11) | −0.0013 (11) | 0.0045 (10) | 0.0016 (10) |
C10A | 0.0148 (12) | 0.0065 (11) | 0.0158 (12) | −0.0014 (9) | 0.0032 (10) | 0.0025 (9) |
C11A | 0.0180 (13) | 0.0177 (13) | 0.0185 (12) | 0.0093 (10) | 0.0059 (10) | 0.0035 (11) |
C12A | 0.0142 (12) | 0.0155 (12) | 0.0160 (12) | 0.0016 (10) | 0.0034 (10) | 0.0024 (10) |
C13A | 0.0145 (12) | 0.0194 (13) | 0.0151 (12) | 0.0021 (10) | 0.0014 (10) | −0.0015 (10) |
C14A | 0.0157 (13) | 0.0234 (14) | 0.0218 (14) | −0.0010 (11) | 0.0011 (11) | 0.0035 (12) |
C15A | 0.0160 (13) | 0.0367 (17) | 0.0208 (14) | −0.0009 (12) | 0.0067 (11) | 0.0025 (13) |
C16A | 0.0194 (14) | 0.0253 (15) | 0.0257 (14) | 0.0087 (12) | 0.0055 (12) | −0.0003 (12) |
C17A | 0.0228 (14) | 0.0177 (13) | 0.0217 (13) | 0.0049 (11) | 0.0019 (11) | 0.0020 (11) |
C18A | 0.0154 (12) | 0.0153 (12) | 0.0150 (12) | −0.0020 (10) | 0.0018 (10) | −0.0017 (10) |
C19A | 0.0121 (12) | 0.0207 (13) | 0.0163 (12) | −0.0012 (11) | −0.0006 (10) | 0.0024 (11) |
C20A | 0.0182 (13) | 0.0202 (14) | 0.0215 (13) | −0.0005 (11) | −0.0008 (11) | 0.0066 (11) |
C21A | 0.0221 (15) | 0.0330 (16) | 0.0277 (15) | −0.0043 (13) | 0.0064 (12) | 0.0139 (14) |
C22A | 0.0209 (14) | 0.0424 (19) | 0.0246 (15) | 0.0024 (13) | 0.0106 (12) | 0.0084 (14) |
C23A | 0.0199 (14) | 0.0279 (16) | 0.0218 (14) | 0.0049 (12) | 0.0039 (11) | 0.0044 (12) |
C24A | 0.0154 (12) | 0.0223 (14) | 0.0101 (11) | 0.0003 (10) | 0.0013 (9) | −0.0010 (10) |
O1B | 0.0298 (11) | 0.0157 (9) | 0.0182 (9) | −0.0009 (8) | 0.0010 (8) | 0.0017 (8) |
O2B | 0.0270 (10) | 0.0158 (10) | 0.0190 (9) | 0.0019 (8) | −0.0049 (8) | −0.0046 (8) |
O3B | 0.0400 (12) | 0.0157 (9) | 0.0169 (9) | −0.0047 (9) | 0.0069 (9) | −0.0040 (8) |
O4B | 0.0492 (13) | 0.0189 (10) | 0.0138 (9) | 0.0041 (10) | 0.0058 (9) | 0.0049 (8) |
O5B | 0.0198 (9) | 0.0151 (9) | 0.0155 (9) | −0.0005 (8) | 0.0034 (7) | 0.0019 (7) |
O6B | 0.0175 (9) | 0.0174 (9) | 0.0168 (9) | −0.0038 (8) | −0.0016 (7) | 0.0022 (8) |
N1B | 0.0199 (11) | 0.0188 (11) | 0.0094 (9) | −0.0042 (9) | 0.0017 (8) | 0.0014 (9) |
N2B | 0.0199 (11) | 0.0153 (11) | 0.0141 (10) | 0.0007 (9) | 0.0013 (9) | −0.0010 (9) |
N3B | 0.0382 (14) | 0.0110 (11) | 0.0177 (11) | −0.0029 (10) | 0.0056 (10) | 0.0026 (9) |
C1B | 0.0201 (13) | 0.0164 (13) | 0.0090 (11) | −0.0032 (10) | 0.0038 (10) | −0.0015 (10) |
C2B | 0.0157 (12) | 0.0162 (12) | 0.0101 (11) | −0.0007 (10) | −0.0002 (10) | −0.0009 (10) |
C3B | 0.0194 (13) | 0.0167 (13) | 0.0160 (12) | −0.0030 (11) | 0.0067 (10) | −0.0050 (11) |
C4B | 0.0166 (12) | 0.0157 (13) | 0.0168 (12) | −0.0018 (10) | 0.0045 (10) | −0.0005 (10) |
C5B | 0.0153 (12) | 0.0141 (12) | 0.0149 (12) | 0.0008 (10) | 0.0036 (10) | 0.0020 (10) |
C6B | 0.0168 (12) | 0.0154 (12) | 0.0109 (11) | −0.0001 (10) | 0.0023 (10) | −0.0021 (10) |
C7B | 0.0185 (13) | 0.0168 (13) | 0.0147 (12) | 0.0008 (10) | 0.0051 (10) | 0.0030 (10) |
C8B | 0.0249 (14) | 0.0197 (13) | 0.0139 (12) | 0.0017 (11) | 0.0062 (11) | 0.0036 (11) |
C9B | 0.0221 (13) | 0.0197 (14) | 0.0128 (12) | −0.0015 (11) | 0.0040 (10) | 0.0013 (10) |
C10B | 0.0201 (13) | 0.0094 (11) | 0.0112 (11) | 0.0038 (10) | 0.0006 (10) | −0.0007 (10) |
C11B | 0.0175 (13) | 0.0215 (14) | 0.0216 (13) | −0.0007 (11) | 0.0031 (11) | −0.0029 (11) |
C12B | 0.0148 (12) | 0.0197 (13) | 0.0197 (13) | −0.0025 (10) | 0.0011 (10) | 0.0017 (11) |
C13B | 0.0169 (13) | 0.0179 (13) | 0.0259 (14) | 0.0013 (11) | 0.0011 (11) | 0.0009 (12) |
C14B | 0.0271 (15) | 0.0317 (17) | 0.0316 (16) | −0.0043 (13) | 0.0112 (13) | −0.0061 (14) |
C15B | 0.0243 (16) | 0.0348 (18) | 0.050 (2) | −0.0052 (14) | 0.0184 (15) | −0.0080 (16) |
C16B | 0.0208 (15) | 0.0250 (16) | 0.061 (2) | −0.0028 (13) | 0.0171 (15) | −0.0164 (16) |
C17B | 0.0194 (14) | 0.0197 (14) | 0.0412 (18) | 0.0016 (12) | 0.0045 (13) | −0.0132 (13) |
C18B | 0.0166 (13) | 0.0140 (12) | 0.0315 (15) | 0.0047 (10) | 0.0040 (12) | −0.0028 (11) |
C19B | 0.0191 (13) | 0.0175 (14) | 0.0271 (14) | 0.0023 (11) | 0.0034 (11) | −0.0033 (12) |
C20B | 0.0225 (15) | 0.0269 (16) | 0.0349 (16) | −0.0003 (12) | 0.0025 (13) | −0.0150 (13) |
C21B | 0.0391 (18) | 0.0296 (17) | 0.0267 (15) | 0.0017 (14) | 0.0104 (14) | −0.0091 (14) |
C22B | 0.0254 (15) | 0.0290 (16) | 0.0338 (16) | 0.0024 (13) | 0.0136 (13) | −0.0037 (14) |
C23B | 0.0251 (14) | 0.0171 (13) | 0.0246 (14) | 0.0024 (11) | 0.0046 (12) | −0.0016 (11) |
C24B | 0.0147 (12) | 0.0119 (12) | 0.0254 (14) | 0.0037 (10) | 0.0000 (11) | 0.0023 (11) |
Cl1 | 0.0563 (6) | 0.0270 (4) | 0.0416 (5) | −0.0115 (4) | −0.0066 (4) | 0.0028 (4) |
Cl2 | 0.0348 (4) | 0.0358 (5) | 0.0546 (5) | −0.0038 (4) | 0.0058 (4) | 0.0124 (4) |
C30 | 0.050 (2) | 0.0354 (19) | 0.0275 (16) | −0.0110 (17) | −0.0089 (15) | 0.0072 (15) |
Cl3 | 0.0529 (16) | 0.0283 (7) | 0.0317 (4) | −0.0087 (12) | −0.0030 (12) | 0.0107 (5) |
Cl4 | 0.0613 (14) | 0.0783 (15) | 0.0718 (12) | −0.0055 (11) | −0.0419 (11) | 0.0307 (11) |
C40 | 0.020 (4) | 0.082 (3) | 0.063 (3) | −0.011 (3) | −0.010 (2) | 0.051 (3) |
Cl31 | 0.0529 (16) | 0.0283 (7) | 0.0317 (4) | −0.0087 (12) | −0.0030 (12) | 0.0107 (5) |
Cl41 | 0.0613 (14) | 0.0783 (15) | 0.0718 (12) | −0.0055 (11) | −0.0419 (11) | 0.0307 (11) |
C401 | 0.020 (4) | 0.082 (3) | 0.063 (3) | −0.011 (3) | −0.010 (2) | 0.051 (3) |
Cl5 | 0.0454 (6) | 0.1205 (11) | 0.0332 (5) | 0.0132 (6) | 0.0137 (4) | −0.0145 (6) |
Cl6 | 0.0818 (8) | 0.0540 (7) | 0.0818 (8) | 0.0010 (6) | −0.0397 (7) | −0.0023 (6) |
C50 | 0.0341 (19) | 0.058 (2) | 0.0319 (17) | −0.0064 (17) | 0.0080 (15) | 0.0009 (17) |
Cl7 | 0.0478 (6) | 0.1219 (12) | 0.0706 (7) | −0.0041 (7) | 0.0167 (6) | −0.0336 (8) |
Cl8 | 0.0946 (9) | 0.0996 (10) | 0.0655 (7) | −0.0368 (8) | 0.0273 (7) | −0.0215 (8) |
C60 | 0.041 (2) | 0.085 (3) | 0.054 (2) | 0.001 (2) | 0.0086 (19) | −0.013 (2) |
Geometric parameters (Å, º) top
O1A—C1A | 1.208 (3) | N1B—H1B | 0.8800 |
O2A—C1A | 1.325 (3) | N2B—C6B | 1.437 (3) |
O2A—H2OA | 0.8400 | N3B—C7B | 1.349 (3) |
O3A—N2A | 1.253 (3) | N3B—H3B1 | 0.8800 |
O4A—N2A | 1.238 (3) | N3B—H3B2 | 0.8800 |
O5A—C10A | 1.235 (3) | C1B—C2B | 1.532 (4) |
O6A—C10A | 1.344 (3) | C2B—C3B | 1.539 (4) |
O6A—C11A | 1.461 (3) | C2B—H2B | 1.0000 |
N1A—C10A | 1.333 (3) | C3B—C4B | 1.513 (4) |
N1A—C2A | 1.456 (3) | C3B—H321 | 0.9900 |
N1A—H1A | 0.8800 | C3B—H322 | 0.9900 |
N2A—C6A | 1.428 (3) | C4B—C5B | 1.372 (4) |
N3A—C7A | 1.342 (3) | C4B—C9B | 1.410 (4) |
N3A—H3A1 | 0.8800 | C5B—C6B | 1.408 (4) |
N3A—H3A2 | 0.8800 | C5B—H5B | 0.9500 |
C1A—C2A | 1.527 (3) | C6B—C7B | 1.421 (4) |
C2A—C3A | 1.544 (4) | C7B—C8B | 1.419 (4) |
C2A—H2A | 1.0000 | C8B—C9B | 1.381 (4) |
C3A—C4A | 1.513 (4) | C8B—H8B | 0.9500 |
C3A—H311 | 0.9900 | C9B—H9B | 0.9500 |
C3A—H312 | 0.9900 | C11B—C12B | 1.532 (4) |
C4A—C5A | 1.376 (3) | C11B—H1B1 | 0.9900 |
C4A—C9A | 1.415 (3) | C11B—H1B2 | 0.9900 |
C5A—C6A | 1.417 (4) | C12B—C24B | 1.521 (4) |
C5A—H5A | 0.9500 | C12B—C13B | 1.524 (4) |
C6A—C7A | 1.415 (4) | C12B—H12B | 1.0000 |
C7A—C8A | 1.427 (4) | C13B—C14B | 1.394 (4) |
C8A—C9A | 1.380 (4) | C13B—C18B | 1.400 (4) |
C8A—H8A | 0.9500 | C14B—C15B | 1.398 (4) |
C9A—H9A | 0.9500 | C14B—H14B | 0.9500 |
C11A—C12A | 1.513 (3) | C15B—C16B | 1.395 (5) |
C11A—H1A1 | 0.9900 | C15B—H15B | 0.9500 |
C11A—H1A2 | 0.9900 | C16B—C17B | 1.389 (5) |
C12A—C24A | 1.520 (4) | C16B—H16B | 0.9500 |
C12A—C13A | 1.526 (4) | C17B—C18B | 1.396 (4) |
C12A—H12A | 1.0000 | C17B—H17B | 0.9500 |
C13A—C14A | 1.382 (4) | C18B—C19B | 1.465 (4) |
C13A—C18A | 1.398 (4) | C19B—C20B | 1.397 (4) |
C14A—C15A | 1.399 (4) | C19B—C24B | 1.408 (4) |
C14A—H14A | 0.9500 | C20B—C21B | 1.387 (5) |
C15A—C16A | 1.395 (4) | C20B—H20B | 0.9500 |
C15A—H15A | 0.9500 | C21B—C22B | 1.390 (4) |
C16A—C17A | 1.391 (4) | C21B—H21B | 0.9500 |
C16A—H16A | 0.9500 | C22B—C23B | 1.395 (4) |
C17A—C18A | 1.393 (4) | C22B—H22B | 0.9500 |
C17A—H17A | 0.9500 | C23B—C24B | 1.396 (4) |
C18A—C19A | 1.470 (4) | C23B—H23B | 0.9500 |
C19A—C24A | 1.396 (4) | Cl1—C30 | 1.771 (3) |
C19A—C20A | 1.398 (4) | Cl2—C30 | 1.783 (4) |
C20A—C21A | 1.390 (4) | C30—H301 | 0.9900 |
C20A—H20A | 0.9500 | C30—H302 | 0.9900 |
C21A—C22A | 1.393 (4) | Cl3—C40 | 1.741 (3) |
C21A—H21A | 0.9500 | Cl4—C40 | 1.735 (4) |
C22A—C23A | 1.395 (4) | C40—H401 | 0.9900 |
C22A—H22A | 0.9500 | C40—H402 | 0.9900 |
C23A—C24A | 1.391 (4) | Cl31—C401 | 1.739 (5) |
C23A—H23A | 0.9500 | Cl41—C401 | 1.737 (5) |
O1B—C1B | 1.212 (3) | C401—H411 | 0.9900 |
O2B—C1B | 1.322 (3) | C401—H412 | 0.9900 |
O2B—H2OB | 0.8400 | Cl5—C50 | 1.758 (4) |
O3B—N2B | 1.252 (3) | Cl6—C50 | 1.736 (4) |
O4B—N2B | 1.236 (3) | C50—H501 | 0.9900 |
O5B—C10B | 1.226 (3) | C50—H502 | 0.9900 |
O6B—C10B | 1.344 (3) | Cl7—C60 | 1.766 (4) |
O6B—C11B | 1.455 (3) | Cl8—C60 | 1.753 (5) |
N1B—C10B | 1.340 (3) | C60—H601 | 0.9900 |
N1B—C2B | 1.451 (3) | C60—H602 | 0.9900 |
| | | |
C1A—O2A—H2OA | 109.5 | N1B—C2B—C3B | 110.9 (2) |
C10A—O6A—C11A | 114.33 (18) | C1B—C2B—C3B | 110.5 (2) |
C10A—N1A—C2A | 120.0 (2) | N1B—C2B—H2B | 108.6 |
C10A—N1A—H1A | 120.0 | C1B—C2B—H2B | 108.6 |
C2A—N1A—H1A | 120.0 | C3B—C2B—H2B | 108.6 |
O4A—N2A—O3A | 120.2 (2) | C4B—C3B—C2B | 112.1 (2) |
O4A—N2A—C6A | 120.4 (2) | C4B—C3B—H321 | 109.2 |
O3A—N2A—C6A | 119.5 (2) | C2B—C3B—H321 | 109.2 |
C7A—N3A—H3A1 | 120.0 | C4B—C3B—H322 | 109.2 |
C7A—N3A—H3A2 | 120.0 | C2B—C3B—H322 | 109.2 |
H3A1—N3A—H3A2 | 120.0 | H321—C3B—H322 | 107.9 |
O1A—C1A—O2A | 124.8 (2) | C5B—C4B—C9B | 117.7 (2) |
O1A—C1A—C2A | 124.3 (2) | C5B—C4B—C3B | 121.4 (2) |
O2A—C1A—C2A | 110.8 (2) | C9B—C4B—C3B | 120.9 (2) |
N1A—C2A—C1A | 111.8 (2) | C4B—C5B—C6B | 121.5 (2) |
N1A—C2A—C3A | 110.78 (19) | C4B—C5B—H5B | 119.3 |
C1A—C2A—C3A | 111.6 (2) | C6B—C5B—H5B | 119.3 |
N1A—C2A—H2A | 107.5 | C5B—C6B—C7B | 121.5 (2) |
C1A—C2A—H2A | 107.5 | C5B—C6B—N2B | 117.2 (2) |
C3A—C2A—H2A | 107.5 | C7B—C6B—N2B | 121.3 (2) |
C4A—C3A—C2A | 109.8 (2) | N3B—C7B—C8B | 118.9 (2) |
C4A—C3A—H311 | 109.7 | N3B—C7B—C6B | 125.2 (2) |
C2A—C3A—H311 | 109.7 | C8B—C7B—C6B | 115.9 (2) |
C4A—C3A—H312 | 109.7 | C9B—C8B—C7B | 121.5 (2) |
C2A—C3A—H312 | 109.7 | C9B—C8B—H8B | 119.3 |
H311—C3A—H312 | 108.2 | C7B—C8B—H8B | 119.3 |
C5A—C4A—C9A | 118.1 (2) | C8B—C9B—C4B | 121.9 (2) |
C5A—C4A—C3A | 121.3 (2) | C8B—C9B—H9B | 119.1 |
C9A—C4A—C3A | 120.6 (2) | C4B—C9B—H9B | 119.0 |
C4A—C5A—C6A | 120.7 (2) | O5B—C10B—N1B | 125.1 (2) |
C4A—C5A—H5A | 119.6 | O5B—C10B—O6B | 123.9 (2) |
C6A—C5A—H5A | 119.6 | N1B—C10B—O6B | 111.0 (2) |
C7A—C6A—C5A | 122.1 (2) | O6B—C11B—C12B | 111.2 (2) |
C7A—C6A—N2A | 121.4 (2) | O6B—C11B—H1B1 | 109.4 |
C5A—C6A—N2A | 116.6 (2) | C12B—C11B—H1B1 | 109.4 |
N3A—C7A—C6A | 125.7 (2) | O6B—C11B—H1B2 | 109.4 |
N3A—C7A—C8A | 118.6 (2) | C12B—C11B—H1B2 | 109.4 |
C6A—C7A—C8A | 115.7 (2) | H1B1—C11B—H1B2 | 108.0 |
C9A—C8A—C7A | 121.7 (2) | C24B—C12B—C13B | 102.0 (2) |
C9A—C8A—H8A | 119.2 | C24B—C12B—C11B | 113.5 (2) |
C7A—C8A—H8A | 119.2 | C13B—C12B—C11B | 109.7 (2) |
C8A—C9A—C4A | 121.7 (2) | C24B—C12B—H12B | 110.4 |
C8A—C9A—H9A | 119.2 | C13B—C12B—H12B | 110.4 |
C4A—C9A—H9A | 119.2 | C11B—C12B—H12B | 110.4 |
O5A—C10A—N1A | 124.2 (2) | C14B—C13B—C18B | 120.8 (3) |
O5A—C10A—O6A | 123.3 (2) | C14B—C13B—C12B | 128.8 (3) |
N1A—C10A—O6A | 112.5 (2) | C18B—C13B—C12B | 110.3 (2) |
O6A—C11A—C12A | 108.7 (2) | C13B—C14B—C15B | 118.6 (3) |
O6A—C11A—H1A1 | 109.9 | C13B—C14B—H14B | 120.7 |
C12A—C11A—H1A1 | 109.9 | C15B—C14B—H14B | 120.7 |
O6A—C11A—H1A2 | 109.9 | C16B—C15B—C14B | 120.2 (3) |
C12A—C11A—H1A2 | 109.9 | C16B—C15B—H15B | 119.9 |
H1A1—C11A—H1A2 | 108.3 | C14B—C15B—H15B | 119.9 |
C11A—C12A—C24A | 115.2 (2) | C17B—C16B—C15B | 121.4 (3) |
C11A—C12A—C13A | 108.8 (2) | C17B—C16B—H16B | 119.3 |
C24A—C12A—C13A | 102.1 (2) | C15B—C16B—H16B | 119.3 |
C11A—C12A—H12A | 110.2 | C16B—C17B—C18B | 118.4 (3) |
C24A—C12A—H12A | 110.2 | C16B—C17B—H17B | 120.8 |
C13A—C12A—H12A | 110.2 | C18B—C17B—H17B | 120.8 |
C14A—C13A—C18A | 121.3 (2) | C17B—C18B—C13B | 120.4 (3) |
C14A—C13A—C12A | 128.6 (2) | C17B—C18B—C19B | 130.8 (3) |
C18A—C13A—C12A | 110.1 (2) | C13B—C18B—C19B | 108.7 (2) |
C13A—C14A—C15A | 118.6 (3) | C20B—C19B—C24B | 120.1 (3) |
C13A—C14A—H14A | 120.7 | C20B—C19B—C18B | 131.2 (3) |
C15A—C14A—H14A | 120.7 | C24B—C19B—C18B | 108.7 (2) |
C16A—C15A—C14A | 120.0 (3) | C21B—C20B—C19B | 119.0 (3) |
C16A—C15A—H15A | 120.0 | C21B—C20B—H20B | 120.5 |
C14A—C15A—H15A | 120.0 | C19B—C20B—H20B | 120.5 |
C17A—C16A—C15A | 121.3 (3) | C20B—C21B—C22B | 120.6 (3) |
C17A—C16A—H16A | 119.3 | C20B—C21B—H21B | 119.7 |
C15A—C16A—H16A | 119.3 | C22B—C21B—H21B | 119.7 |
C16A—C17A—C18A | 118.3 (3) | C21B—C22B—C23B | 121.3 (3) |
C16A—C17A—H17A | 120.8 | C21B—C22B—H22B | 119.4 |
C18A—C17A—H17A | 120.8 | C23B—C22B—H22B | 119.4 |
C17A—C18A—C13A | 120.3 (2) | C22B—C23B—C24B | 118.2 (3) |
C17A—C18A—C19A | 131.0 (3) | C22B—C23B—H23B | 120.9 |
C13A—C18A—C19A | 108.7 (2) | C24B—C23B—H23B | 120.9 |
C24A—C19A—C20A | 120.3 (2) | C23B—C24B—C19B | 120.7 (3) |
C24A—C19A—C18A | 108.8 (2) | C23B—C24B—C12B | 129.2 (2) |
C20A—C19A—C18A | 130.9 (3) | C19B—C24B—C12B | 110.1 (2) |
C21A—C20A—C19A | 119.0 (3) | Cl1—C30—Cl2 | 110.92 (19) |
C21A—C20A—H20A | 120.5 | Cl1—C30—H301 | 109.5 |
C19A—C20A—H20A | 120.5 | Cl2—C30—H301 | 109.5 |
C20A—C21A—C22A | 120.3 (3) | Cl1—C30—H302 | 109.5 |
C20A—C21A—H21A | 119.9 | Cl2—C30—H302 | 109.5 |
C22A—C21A—H21A | 119.9 | H301—C30—H302 | 108.0 |
C21A—C22A—C23A | 121.1 (3) | Cl4—C40—Cl3 | 116.6 (4) |
C21A—C22A—H22A | 119.4 | Cl4—C40—H401 | 108.1 |
C23A—C22A—H22A | 119.4 | Cl3—C40—H401 | 108.1 |
C24A—C23A—C22A | 118.4 (3) | Cl4—C40—H402 | 108.1 |
C24A—C23A—H23A | 120.8 | Cl3—C40—H402 | 108.1 |
C22A—C23A—H23A | 120.8 | H401—C40—H402 | 107.3 |
C23A—C24A—C19A | 120.9 (3) | Cl41—C401—Cl31 | 108.6 (9) |
C23A—C24A—C12A | 128.8 (2) | Cl41—C401—H411 | 110.0 |
C19A—C24A—C12A | 110.3 (2) | Cl31—C401—H411 | 110.0 |
C1B—O2B—H2OB | 109.5 | Cl41—C401—H412 | 110.0 |
C10B—O6B—C11B | 116.2 (2) | Cl31—C401—H412 | 110.0 |
C10B—N1B—C2B | 122.4 (2) | H411—C401—H412 | 108.3 |
C10B—N1B—H1B | 118.8 | Cl6—C50—Cl5 | 112.2 (2) |
C2B—N1B—H1B | 118.8 | Cl6—C50—H501 | 109.2 |
O4B—N2B—O3B | 121.2 (2) | Cl5—C50—H501 | 109.2 |
O4B—N2B—C6B | 119.5 (2) | Cl6—C50—H502 | 109.2 |
O3B—N2B—C6B | 119.3 (2) | Cl5—C50—H502 | 109.2 |
C7B—N3B—H3B1 | 120.0 | H501—C50—H502 | 107.9 |
C7B—N3B—H3B2 | 120.0 | Cl8—C60—Cl7 | 112.7 (2) |
H3B1—N3B—H3B2 | 120.0 | Cl8—C60—H601 | 109.1 |
O1B—C1B—O2B | 124.5 (2) | Cl7—C60—H601 | 109.1 |
O1B—C1B—C2B | 123.7 (2) | Cl8—C60—H602 | 109.1 |
O2B—C1B—C2B | 111.8 (2) | Cl7—C60—H602 | 109.1 |
N1B—C2B—C1B | 109.7 (2) | H601—C60—H602 | 107.8 |
| | | |
C10A—N1A—C2A—C1A | −114.1 (2) | C10B—N1B—C2B—C1B | −110.1 (3) |
C10A—N1A—C2A—C3A | 120.7 (2) | C10B—N1B—C2B—C3B | 127.5 (2) |
O1A—C1A—C2A—N1A | −4.5 (4) | O1B—C1B—C2B—N1B | −7.3 (3) |
O2A—C1A—C2A—N1A | 174.0 (2) | O2B—C1B—C2B—N1B | 173.8 (2) |
O1A—C1A—C2A—C3A | 120.2 (3) | O1B—C1B—C2B—C3B | 115.3 (3) |
O2A—C1A—C2A—C3A | −61.3 (3) | O2B—C1B—C2B—C3B | −63.6 (3) |
N1A—C2A—C3A—C4A | −55.7 (3) | N1B—C2B—C3B—C4B | −56.2 (3) |
C1A—C2A—C3A—C4A | 179.0 (2) | C1B—C2B—C3B—C4B | −178.1 (2) |
C2A—C3A—C4A—C5A | 113.4 (3) | C2B—C3B—C4B—C5B | 103.9 (3) |
C2A—C3A—C4A—C9A | −64.6 (3) | C2B—C3B—C4B—C9B | −74.3 (3) |
C9A—C4A—C5A—C6A | 0.6 (4) | C9B—C4B—C5B—C6B | −0.8 (4) |
C3A—C4A—C5A—C6A | −177.5 (2) | C3B—C4B—C5B—C6B | −179.1 (2) |
C4A—C5A—C6A—C7A | 0.6 (4) | C4B—C5B—C6B—C7B | 2.5 (4) |
C4A—C5A—C6A—N2A | 179.5 (2) | C4B—C5B—C6B—N2B | −175.9 (2) |
O4A—N2A—C6A—C7A | 173.2 (2) | O4B—N2B—C6B—C5B | −2.0 (4) |
O3A—N2A—C6A—C7A | −7.9 (4) | O3B—N2B—C6B—C5B | 175.9 (2) |
O4A—N2A—C6A—C5A | −5.7 (4) | O4B—N2B—C6B—C7B | 179.7 (2) |
O3A—N2A—C6A—C5A | 173.1 (2) | O3B—N2B—C6B—C7B | −2.5 (4) |
C5A—C6A—C7A—N3A | 178.7 (3) | C5B—C6B—C7B—N3B | 178.8 (3) |
N2A—C6A—C7A—N3A | −0.1 (4) | N2B—C6B—C7B—N3B | −2.9 (4) |
C5A—C6A—C7A—C8A | −1.2 (4) | C5B—C6B—C7B—C8B | −2.6 (4) |
N2A—C6A—C7A—C8A | 180.0 (2) | N2B—C6B—C7B—C8B | 175.7 (2) |
N3A—C7A—C8A—C9A | −179.3 (2) | N3B—C7B—C8B—C9B | 179.9 (3) |
C6A—C7A—C8A—C9A | 0.6 (4) | C6B—C7B—C8B—C9B | 1.2 (4) |
C7A—C8A—C9A—C4A | 0.6 (4) | C7B—C8B—C9B—C4B | 0.4 (4) |
C5A—C4A—C9A—C8A | −1.2 (4) | C5B—C4B—C9B—C8B | −0.6 (4) |
C3A—C4A—C9A—C8A | 177.0 (2) | C3B—C4B—C9B—C8B | 177.6 (2) |
C2A—N1A—C10A—O5A | 13.3 (4) | C2B—N1B—C10B—O5B | −0.1 (4) |
C2A—N1A—C10A—O6A | −166.6 (2) | C2B—N1B—C10B—O6B | 179.1 (2) |
C11A—O6A—C10A—O5A | −0.9 (3) | C11B—O6B—C10B—O5B | −4.1 (4) |
C11A—O6A—C10A—N1A | 179.1 (2) | C11B—O6B—C10B—N1B | 176.7 (2) |
C10A—O6A—C11A—C12A | −175.2 (2) | C10B—O6B—C11B—C12B | −83.6 (3) |
O6A—C11A—C12A—C24A | 65.5 (3) | O6B—C11B—C12B—C24B | −62.4 (3) |
O6A—C11A—C12A—C13A | 179.3 (2) | O6B—C11B—C12B—C13B | −175.8 (2) |
C11A—C12A—C13A—C14A | 59.0 (3) | C24B—C12B—C13B—C14B | 177.8 (3) |
C24A—C12A—C13A—C14A | −178.9 (3) | C11B—C12B—C13B—C14B | −61.5 (4) |
C11A—C12A—C13A—C18A | −121.3 (2) | C24B—C12B—C13B—C18B | −3.4 (3) |
C24A—C12A—C13A—C18A | 0.9 (3) | C11B—C12B—C13B—C18B | 117.3 (3) |
C18A—C13A—C14A—C15A | 0.1 (4) | C18B—C13B—C14B—C15B | 1.0 (5) |
C12A—C13A—C14A—C15A | 179.8 (2) | C12B—C13B—C14B—C15B | 179.7 (3) |
C13A—C14A—C15A—C16A | −1.2 (4) | C13B—C14B—C15B—C16B | −1.2 (5) |
C14A—C15A—C16A—C17A | 1.8 (4) | C14B—C15B—C16B—C17B | −0.6 (5) |
C15A—C16A—C17A—C18A | −1.2 (4) | C15B—C16B—C17B—C18B | 2.5 (5) |
C16A—C17A—C18A—C13A | 0.0 (4) | C16B—C17B—C18B—C13B | −2.7 (4) |
C16A—C17A—C18A—C19A | −178.5 (3) | C16B—C17B—C18B—C19B | 176.7 (3) |
C14A—C13A—C18A—C17A | 0.6 (4) | C14B—C13B—C18B—C17B | 1.0 (4) |
C12A—C13A—C18A—C17A | −179.2 (2) | C12B—C13B—C18B—C17B | −177.9 (2) |
C14A—C13A—C18A—C19A | 179.3 (2) | C14B—C13B—C18B—C19B | −178.6 (3) |
C12A—C13A—C18A—C19A | −0.4 (3) | C12B—C13B—C18B—C19B | 2.5 (3) |
C17A—C18A—C19A—C24A | 178.4 (3) | C17B—C18B—C19B—C20B | −0.3 (5) |
C13A—C18A—C19A—C24A | −0.2 (3) | C13B—C18B—C19B—C20B | 179.2 (3) |
C17A—C18A—C19A—C20A | 0.2 (5) | C17B—C18B—C19B—C24B | −179.9 (3) |
C13A—C18A—C19A—C20A | −178.4 (3) | C13B—C18B—C19B—C24B | −0.4 (3) |
C24A—C19A—C20A—C21A | 0.5 (4) | C24B—C19B—C20B—C21B | 0.1 (4) |
C18A—C19A—C20A—C21A | 178.6 (3) | C18B—C19B—C20B—C21B | −179.5 (3) |
C19A—C20A—C21A—C22A | 0.1 (4) | C19B—C20B—C21B—C22B | −0.2 (5) |
C20A—C21A—C22A—C23A | 0.0 (5) | C20B—C21B—C22B—C23B | 0.7 (5) |
C21A—C22A—C23A—C24A | −0.7 (4) | C21B—C22B—C23B—C24B | −1.1 (4) |
C22A—C23A—C24A—C19A | 1.3 (4) | C22B—C23B—C24B—C19B | 1.0 (4) |
C22A—C23A—C24A—C12A | −179.3 (3) | C22B—C23B—C24B—C12B | −177.9 (3) |
C20A—C19A—C24A—C23A | −1.3 (4) | C20B—C19B—C24B—C23B | −0.5 (4) |
C18A—C19A—C24A—C23A | −179.7 (2) | C18B—C19B—C24B—C23B | 179.2 (2) |
C20A—C19A—C24A—C12A | 179.3 (2) | C20B—C19B—C24B—C12B | 178.5 (3) |
C18A—C19A—C24A—C12A | 0.8 (3) | C18B—C19B—C24B—C12B | −1.8 (3) |
C11A—C12A—C24A—C23A | −62.7 (4) | C13B—C12B—C24B—C23B | −178.0 (3) |
C13A—C12A—C24A—C23A | 179.6 (3) | C11B—C12B—C24B—C23B | 64.1 (4) |
C11A—C12A—C24A—C19A | 116.7 (2) | C13B—C12B—C24B—C19B | 3.1 (3) |
C13A—C12A—C24A—C19A | −1.0 (3) | C11B—C12B—C24B—C19B | −114.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2OA···O5Ai | 0.84 | 1.80 | 2.631 (3) | 173 |
N1A—H1A···O3B | 0.88 | 2.35 | 3.134 (3) | 148 |
N3A—H3A1···O3A | 0.88 | 2.03 | 2.643 (3) | 126 |
N3A—H3A1···O4Bii | 0.88 | 2.32 | 2.958 (3) | 129 |
N3A—H3A2···O1Aii | 0.88 | 2.08 | 2.932 (3) | 163 |
O2B—H2OB···O5Biii | 0.84 | 1.83 | 2.669 (3) | 178 |
N1B—H1B···O3Aiv | 0.88 | 2.37 | 3.186 (3) | 154 |
N3B—H3B2···O3B | 0.88 | 2.01 | 2.630 (3) | 126 |
N3B—H3B2···O4A | 0.88 | 2.39 | 2.942 (3) | 121 |
N3B—H3B1···O1Bii | 0.88 | 2.13 | 2.977 (3) | 161 |
C5B—H5B···O3Aiv | 0.95 | 2.50 | 3.277 (3) | 139 |
C8B—H8B···O5Bv | 0.95 | 2.41 | 3.326 (3) | 162 |
C30—H301···O1Avi | 0.99 | 2.49 | 3.170 (4) | 125 |
C40—H401···O4Aiii | 0.99 | 2.35 | 3.239 (7) | 149 |
Symmetry codes: (i) −x+1, y+1/2, −z; (ii) x, y−1, z; (iii) −x+1, y+1/2, −z+1; (iv) x, y+1, z; (v) −x+1, y−1/2, −z+1; (vi) x−1, y, z. |
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