Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014831/lh6080sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014831/lh6080Isup2.hkl |
CCDC reference: 221683
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.015 Å
- R factor = 0.089
- wR factor = 0.193
- Data-to-parameter ratio = 9.8
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
ATOM_007 Alert A _atom_site_aniso_label is missing Unique label identifying the atom site.
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54184 PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C133 - C134 = 1.37 Ang. PLAT_360 Alert C Short C(sp3)-C(sp3) Bond C134 - C135 = 1.43 Ang. General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 68.25 From the CIF: _reflns_number_total 3190 Count of symmetry unique reflns 3258 Completeness (_total/calc) 97.91% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no 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.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: RAPID-AUTO (Rigaku/MSC and Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.
C14H24N2O5 | F(000) = 648.00 |
Mr = 300.35 | ? # Insert any comments here. |
Monoclinic, P21 | Dx = 1.190 Mg m−3 |
Hall symbol: P 2yb | Cu Kα radiation, λ = 1.54184 Å |
a = 10.131 (5) Å | Cell parameters from 4739 reflections |
b = 9.940 (5) Å | θ = 6.3–62.2° |
c = 16.784 (8) Å | µ = 0.75 mm−1 |
β = 97.33 (3)° | T = 173 K |
V = 1676.4 (14) Å3 | Platelet, colorless |
Z = 4 | 0.20 × 0.20 × 0.10 mm |
Rigaku RAXIS-RAPID diffractometer | 2122 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.040 |
ω scans | θmax = 68.3° |
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983) | h = −12→11 |
Tmin = 0.841, Tmax = 0.928 | k = −11→11 |
31310 measured reflections | l = −19→19 |
3190 independent reflections |
Refinement on F2 | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.089 | w = 1/[0.001Fo2 + 3σ(Fo2) + 0.5]/(4Fo2) |
wR(F2) = 0.193 | (Δ/σ)max = 0.007 |
S = 1.76 | Δρmax = 0.59 e Å−3 |
2134 reflections | Δρmin = −0.33 e Å−3 |
217 parameters |
Experimental. ? #Insert any special details here. |
Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
O(111) | 0.0826 (6) | 0.3912 (6) | 0.3556 (4) | 0.0543 (17)* | |
O(112) | 0.1819 (7) | 0.1928 (7) | 0.3247 (4) | 0.0682 (19)* | |
O(121) | 0.0686 (6) | 0.5082 (7) | 0.1774 (4) | 0.0631 (19)* | |
O(131) | 0.0892 (6) | 0.8114 (7) | 0.0994 (4) | 0.0619 (18)* | |
O(141) | −0.1319 (6) | 0.8192 (7) | 0.0673 (4) | 0.0553 (17)* | |
O(211) | 0.4687 (5) | −0.0359 (7) | 0.3815 (3) | 0.0537 (16)* | |
O(212) | 0.6203 (7) | −0.0349 (7) | 0.2908 (4) | 0.0679 (19)* | |
O(221) | 0.4898 (6) | 0.3141 (7) | 0.2287 (4) | 0.0649 (19)* | |
O(231) | 0.4858 (6) | 0.4659 (6) | 0.0570 (4) | 0.0599 (16)* | |
O(241) | 0.6296 (6) | 0.5991 (7) | 0.1347 (3) | 0.0502 (16)* | |
N(121) | 0.2623 (8) | 0.3972 (8) | 0.2933 (5) | 0.057 (2)* | |
N(131) | 0.0617 (7) | 0.6983 (8) | 0.2484 (4) | 0.049 (2)* | |
N(221) | 0.4122 (8) | 0.0475 (8) | 0.2588 (4) | 0.054 (2)* | |
N(231) | 0.6141 (6) | 0.2397 (7) | 0.1385 (4) | 0.0382 (16)* | |
C(111) | −0.0376 (10) | 0.3283 (11) | 0.3802 (6) | 0.062 (3)* | |
C(112) | −0.0021 (11) | 0.2469 (13) | 0.4552 (6) | 0.090 (4)* | |
C(113) | −0.1102 (10) | 0.2474 (12) | 0.3155 (6) | 0.073 (3)* | |
C(114) | −0.1223 (10) | 0.4522 (14) | 0.3946 (8) | 0.106 (4)* | |
C(115) | 0.1766 (9) | 0.3176 (11) | 0.3252 (6) | 0.054 (3)* | |
C(121) | 0.2450 (8) | 0.5432 (9) | 0.2858 (5) | 0.048 (2)* | |
C(122) | 0.1167 (8) | 0.5783 (10) | 0.2340 (5) | 0.043 (2)* | |
C(123) | 0.3615 (8) | 0.6009 (10) | 0.2476 (5) | 0.058 (3)* | |
C(131) | −0.0510 (9) | 0.7498 (11) | 0.1981 (6) | 0.062 (3)* | |
C(132) | −0.0231 (9) | 0.7947 (9) | 0.1171 (5) | 0.049 (2)* | |
C(133) | −0.0851 (14) | 0.8766 (16) | 0.2457 (8) | 0.118 (5)* | |
C(134) | −0.0059 (15) | 0.8791 (18) | 0.3180 (10) | 0.141 (6)* | |
C(135) | 0.1017 (11) | 0.7855 (11) | 0.3172 (7) | 0.074 (3)* | |
C(141) | −0.1183 (9) | 0.8733 (10) | −0.0114 (5) | 0.058 (3)* | |
C(211) | 0.5611 (9) | −0.0946 (10) | 0.4472 (5) | 0.052 (3)* | |
C(212) | 0.6760 (9) | −0.0007 (10) | 0.4702 (6) | 0.066 (3)* | |
C(213) | 0.6065 (9) | −0.2327 (10) | 0.4239 (6) | 0.068 (3)* | |
C(214) | 0.4750 (10) | −0.1080 (12) | 0.5116 (6) | 0.074 (3)* | |
C(215) | 0.5087 (9) | −0.0101 (10) | 0.3089 (5) | 0.049 (2)* | |
C(221) | 0.4379 (9) | 0.0903 (11) | 0.1798 (5) | 0.054 (2)* | |
C(222) | 0.5182 (8) | 0.2206 (9) | 0.1839 (5) | 0.045 (2)* | |
C(223) | 0.3069 (9) | 0.1146 (11) | 0.1260 (6) | 0.067 (3)* | |
C(231) | 0.6787 (8) | 0.3714 (8) | 0.1354 (5) | 0.039 (2)* | |
C(232) | 0.5838 (9) | 0.4799 (10) | 0.1048 (5) | 0.048 (2)* | |
C(233) | 0.7847 (10) | 0.3498 (10) | 0.0796 (6) | 0.062 (3)* | |
C(234) | 0.8126 (10) | 0.1978 (11) | 0.0849 (6) | 0.066 (3)* | |
C(235) | 0.6784 (8) | 0.1357 (9) | 0.0951 (5) | 0.046 (2)* | |
C(241) | 0.5571 (9) | 0.7189 (10) | 0.1029 (6) | 0.062 (3)* | |
H(1) | −0.0803 | 0.2069 | 0.4704 | 0.108* | |
H(2) | 0.0594 | 0.1786 | 0.4455 | 0.108* | |
H(3) | 0.0369 | 0.3039 | 0.4971 | 0.108* | |
H(4) | −0.1932 | 0.2200 | 0.3309 | 0.087* | |
H(5) | −0.1253 | 0.2997 | 0.2678 | 0.087* | |
H(6) | −0.0592 | 0.1701 | 0.3060 | 0.087* | |
H(7) | −0.0754 | 0.5068 | 0.4353 | 0.127* | |
H(8) | −0.1397 | 0.5025 | 0.3463 | 0.126* | |
H(9) | −0.2039 | 0.4237 | 0.4113 | 0.127* | |
H(10) | 0.3379 | 0.3574 | 0.2746 | 0.068* | |
H(11) | 0.2445 | 0.5814 | 0.3377 | 0.058* | |
H(12) | 0.4426 | 0.5792 | 0.2799 | 0.070* | |
H(13) | 0.3617 | 0.5634 | 0.1955 | 0.070* | |
H(14) | 0.3527 | 0.6958 | 0.2434 | 0.070* | |
H(15) | −0.1223 | 0.6870 | 0.1937 | 0.074* | |
H(16) | −0.0700 | 0.9552 | 0.2159 | 0.142* | |
H(17) | −0.1759 | 0.8734 | 0.2544 | 0.142* | |
H(18) | 0.0292 | 0.9671 | 0.3275 | 0.169* | |
H(19) | −0.0571 | 0.8553 | 0.3595 | 0.169* | |
H(20) | 0.1135 | 0.7345 | 0.3655 | 0.089* | |
H(21) | 0.1820 | 0.8313 | 0.3110 | 0.089* | |
H(22) | −0.0732 | 0.9572 | −0.0057 | 0.070* | |
H(23) | −0.0688 | 0.8121 | −0.0394 | 0.070* | |
H(24) | −0.2040 | 0.8857 | −0.0407 | 0.070* | |
H(25) | 0.7353 | −0.0397 | 0.5123 | 0.079* | |
H(26) | 0.7216 | 0.0145 | 0.4250 | 0.079* | |
H(27) | 0.6436 | 0.0824 | 0.4879 | 0.079* | |
H(28) | 0.5311 | −0.2866 | 0.4054 | 0.081* | |
H(29) | 0.6615 | −0.2241 | 0.3824 | 0.081* | |
H(30) | 0.6555 | −0.2746 | 0.4693 | 0.081* | |
H(31) | 0.4431 | −0.0218 | 0.5244 | 0.089* | |
H(32) | 0.4018 | −0.1649 | 0.4939 | 0.089* | |
H(33) | 0.5249 | −0.1458 | 0.5580 | 0.089* | |
H(34) | 0.3266 | 0.0605 | 0.2750 | 0.065* | |
H(35) | 0.4863 | 0.0218 | 0.1567 | 0.064* | |
H(36) | 0.2577 | 0.183 | 0.1489 | 0.081* | |
H(37) | 0.3249 | 0.1425 | 0.0743 | 0.081* | |
H(38) | 0.2566 | 0.0337 | 0.1211 | 0.081* | |
H(39) | 0.7205 | 0.3946 | 0.1875 | 0.047* | |
H(40) | 0.7522 | 0.3752 | 0.0262 | 0.074* | |
H(41) | 0.8628 | 0.3996 | 0.0975 | 0.074* | |
H(42) | 0.8434 | 0.1661 | 0.0372 | 0.079* | |
H(43) | 0.8766 | 0.1775 | 0.1297 | 0.079* | |
H(44) | 0.6893 | 0.0549 | 0.1255 | 0.056* | |
H(45) | 0.6284 | 0.1176 | 0.0444 | 0.056* | |
H(46) | 0.5975 | 0.7969 | 0.1281 | 0.074* | |
H(47) | 0.5594 | 0.7241 | 0.0466 | 0.074* | |
H(48) | 0.4673 | 0.7133 | 0.1134 | 0.074* |
O(111)—C(111) | 1.474 (12) | C(131)—C(133) | 1.555 (18) |
O(111)—C(115) | 1.351 (12) | C(131)—H(15) | 0.95 |
O(112)—C(115) | 1.242 (13) | C(133)—C(134) | 1.37 (2) |
O(121)—C(122) | 1.228 (11) | C(133)—H(16) | 0.95 |
O(131)—C(132) | 1.223 (11) | C(133)—H(17) | 0.95 |
O(141)—C(132) | 1.318 (11) | C(134)—C(135) | 1.43 (2) |
O(141)—C(141) | 1.449 (11) | C(134)—H(18) | 0.95 |
O(211)—C(211) | 1.473 (10) | C(134)—H(19) | 0.95 |
O(211)—C(215) | 1.357 (10) | C(135)—H(20) | 0.95 |
O(212)—C(215) | 1.232 (12) | C(135)—H(21) | 0.95 |
O(221)—C(222) | 1.252 (11) | C(141)—H(22) | 0.95 |
O(231)—C(232) | 1.202 (11) | C(141)—H(23) | 0.95 |
O(241)—C(232) | 1.346 (12) | C(141)—H(24) | 0.95 |
O(241)—C(241) | 1.464 (12) | C(211)—C(212) | 1.504 (13) |
N(121)—C(115) | 1.336 (13) | C(211)—C(213) | 1.515 (14) |
N(121)—C(121) | 1.465 (12) | C(211)—C(214) | 1.479 (13) |
N(121)—H(10) | 0.95 | C(212)—H(25) | 0.95 |
N(131)—C(122) | 1.351 (12) | C(212)—H(26) | 0.95 |
N(131)—C(131) | 1.426 (12) | C(212)—H(27) | 0.95 |
N(131)—C(135) | 1.459 (13) | C(213)—H(28) | 0.95 |
N(221)—C(215) | 1.335 (12) | C(213)—H(29) | 0.95 |
N(221)—C(221) | 1.447 (11) | C(213)—H(30) | 0.95 |
N(221)—H(34) | 0.95 | C(214)—H(31) | 0.95 |
N(231)—C(222) | 1.323 (10) | C(214)—H(32) | 0.95 |
N(231)—C(231) | 1.467 (11) | C(214)—H(33) | 0.95 |
N(231)—C(235) | 1.464 (11) | C(221)—C(222) | 1.526 (14) |
C(111)—C(112) | 1.501 (15) | C(221)—C(223) | 1.526 (13) |
C(111)—C(113) | 1.471 (15) | C(221)—H(35) | 0.95 |
C(111)—C(114) | 1.538 (17) | C(223)—H(36) | 0.95 |
C(112)—H(1) | 0.95 | C(223)—H(37) | 0.95 |
C(112)—H(2) | 0.95 | C(223)—H(38) | 0.95 |
C(112)—H(3) | 0.95 | C(231)—C(232) | 1.492 (12) |
C(113)—H(4) | 0.95 | C(231)—C(233) | 1.527 (13) |
C(113)—H(5) | 0.95 | C(231)—H(39) | 0.95 |
C(113)—H(6) | 0.95 | C(233)—C(234) | 1.538 (15) |
C(114)—H(7) | 0.95 | C(233)—H(40) | 0.95 |
C(114)—H(8) | 0.95 | C(233)—H(41) | 0.95 |
C(114)—H(9) | 0.95 | C(234)—C(235) | 1.523 (13) |
C(121)—C(122) | 1.510 (12) | C(234)—H(42) | 0.95 |
C(121)—C(123) | 1.525 (12) | C(234)—H(43) | 0.95 |
C(121)—H(11) | 0.95 | C(235)—H(44) | 0.95 |
C(123)—H(12) | 0.95 | C(235)—H(45) | 0.95 |
C(123)—H(13) | 0.95 | C(241)—H(46) | 0.95 |
C(123)—H(14) | 0.95 | C(241)—H(47) | 0.95 |
C(131)—C(132) | 1.492 (13) | C(241)—H(48) | 0.95 |
C(111)—O(111)—C(115) | 121.6 (8) | H(21)—C(135)—C(134) | 110.7 |
C(132)—O(141)—C(141) | 118.5 (7) | N(131)—C(135)—C(134) | 105.0 (10) |
C(211)—O(211)—C(215) | 120.9 (7) | H(22)—C(141)—H(23) | 109.5 |
C(232)—O(241)—C(241) | 116.6 (6) | H(22)—C(141)—H(24) | 109.5 |
C(115)—N(121)—C(121) | 122.9 (8) | H(22)—C(141)—O(141) | 109.6 |
C(115)—N(121)—H(10) | 118.6 | H(23)—C(141)—H(24) | 109.5 |
C(121)—N(121)—H(10) | 118.5 | H(23)—C(141)—O(141) | 109.3 |
C(122)—N(131)—C(131) | 121.9 (7) | H(24)—C(141)—O(141) | 109.5 |
C(122)—N(131)—C(135) | 126.0 (7) | C(212)—C(211)—C(213) | 112.2 (8) |
C(131)—N(131)—C(135) | 112.1 (8) | C(212)—C(211)—C(214) | 112.2 (8) |
C(215)—N(221)—C(221) | 120.1 (8) | C(212)—C(211)—O(211) | 110.1 (8) |
C(215)—N(221)—H(34) | 120.0 | C(213)—C(211)—C(214) | 109.5 (9) |
C(221)—N(221)—H(34) | 119.9 | C(213)—C(211)—O(211) | 110.5 (7) |
C(222)—N(231)—C(231) | 120.9 (7) | C(214)—C(211)—O(211) | 101.8 (7) |
C(222)—N(231)—C(235) | 126.2 (7) | H(25)—C(212)—H(26) | 109.5 |
C(231)—N(231)—C(235) | 112.5 (6) | H(25)—C(212)—H(27) | 109.5 |
C(112)—C(111)—C(113) | 111.6 (9) | H(25)—C(212)—C(211) | 109.5 |
C(112)—C(111)—C(114) | 112.2 (9) | H(26)—C(212)—H(27) | 109.5 |
C(112)—C(111)—O(111) | 110.2 (8) | H(26)—C(212)—C(211) | 109.5 |
C(113)—C(111)—C(114) | 108.5 (9) | H(27)—C(212)—C(211) | 109.5 |
C(113)—C(111)—O(111) | 112.3 (8) | H(28)—C(213)—H(29) | 109.5 |
C(114)—C(111)—O(111) | 101.7 (9) | H(28)—C(213)—H(30) | 109.5 |
H(1)—C(112)—H(2) | 109.5 | H(28)—C(213)—C(211) | 109.5 |
H(1)—C(112)—H(3) | 109.5 | H(29)—C(213)—H(30) | 109.5 |
H(1)—C(112)—C(111) | 109.5 | H(29)—C(213)—C(211) | 109.5 |
H(2)—C(112)—H(3) | 109.5 | H(30)—C(213)—C(211) | 109.5 |
H(2)—C(112)—C(111) | 109.5 | H(31)—C(214)—H(32) | 109.5 |
H(3)—C(112)—C(111) | 109.5 | H(31)—C(214)—H(33) | 109.5 |
H(4)—C(113)—H(5) | 109.5 | H(31)—C(214)—C(211) | 109.5 |
H(4)—C(113)—H(6) | 109.5 | H(32)—C(214)—H(33) | 109.5 |
H(4)—C(113)—C(111) | 109.4 | H(32)—C(214)—C(211) | 109.5 |
H(5)—C(113)—H(6) | 109.5 | H(33)—C(214)—C(211) | 109.5 |
H(5)—C(113)—C(111) | 109.5 | O(211)—C(215)—O(212) | 124.9 (8) |
H(6)—C(113)—C(111) | 109.5 | O(211)—C(215)—N(221) | 111.7 (8) |
H(7)—C(114)—H(8) | 109.5 | O(212)—C(215)—N(221) | 123.4 (8) |
H(7)—C(114)—H(9) | 109.5 | C(222)—C(221)—C(223) | 108.1 (8) |
H(7)—C(114)—C(111) | 109.5 | C(222)—C(221)—H(35) | 109.1 |
H(8)—C(114)—H(9) | 109.5 | C(222)—C(221)—N(221) | 111.4 (7) |
H(8)—C(114)—C(111) | 109.5 | C(223)—C(221)—H(35) | 109.1 |
H(9)—C(114)—C(111) | 109.4 | C(223)—C(221)—N(221) | 110.2 (7) |
O(111)—C(115)—O(112) | 125.1 (9) | H(35)—C(221)—N(221) | 109.0 |
O(111)—C(115)—N(121) | 110.9 (9) | O(221)—C(222)—N(231) | 118.8 (8) |
O(112)—C(115)—N(121) | 123.9 (9) | O(221)—C(222)—C(221) | 119.7 (8) |
C(122)—C(121)—C(123) | 109.0 (7) | N(231)—C(222)—C(221) | 121.5 (8) |
C(122)—C(121)—H(11) | 109.3 | H(36)—C(223)—H(37) | 109.5 |
C(122)—C(121)—N(121) | 111.3 (7) | H(36)—C(223)—H(38) | 109.5 |
C(123)—C(121)—H(11) | 109.3 | H(36)—C(223)—C(221) | 109.5 |
C(123)—C(121)—N(121) | 108.5 (7) | H(37)—C(223)—H(38) | 109.5 |
H(11)—C(121)—N(121) | 109.3 | H(37)—C(223)—C(221) | 109.5 |
O(121)—C(122)—N(131) | 120.5 (7) | H(38)—C(223)—C(221) | 109.4 |
O(121)—C(122)—C(121) | 122.9 (8) | C(232)—C(231)—C(233) | 111.3 (7) |
N(131)—C(122)—C(121) | 116.4 (7) | C(232)—C(231)—H(39) | 109.4 |
H(12)—C(123)—H(13) | 109.5 | C(232)—C(231)—N(231) | 112.7 (7) |
H(12)—C(123)—H(14) | 109.5 | C(233)—C(231)—H(39) | 109.4 |
H(12)—C(123)—C(121) | 109.5 | C(233)—C(231)—N(231) | 104.4 (7) |
H(13)—C(123)—H(14) | 109.5 | H(39)—C(231)—N(231) | 109.4 |
H(13)—C(123)—C(121) | 109.4 | O(231)—C(232)—O(241) | 124.5 (9) |
H(14)—C(123)—C(121) | 109.5 | O(231)—C(232)—C(231) | 125.9 (9) |
C(132)—C(131)—C(133) | 107.8 (9) | O(241)—C(232)—C(231) | 109.4 (7) |
C(132)—C(131)—H(15) | 110.8 | C(234)—C(233)—H(40) | 110.9 |
C(132)—C(131)—N(131) | 114.6 (8) | C(234)—C(233)—H(41) | 110.8 |
C(133)—C(131)—H(15) | 110.9 | C(234)—C(233)—C(231) | 104.0 (8) |
C(133)—C(131)—N(131) | 101.6 (8) | H(40)—C(233)—H(41) | 109.5 |
H(15)—C(131)—N(131) | 110.7 | H(40)—C(233)—C(231) | 110.8 |
O(131)—C(132)—O(141) | 123.3 (8) | H(41)—C(233)—C(231) | 110.8 |
O(131)—C(132)—C(131) | 123.5 (8) | C(235)—C(234)—H(42) | 110.7 |
O(141)—C(132)—C(131) | 113.1 (8) | C(235)—C(234)—H(43) | 110.8 |
C(134)—C(133)—H(16) | 109.7 | C(235)—C(234)—C(233) | 104.2 (8) |
C(134)—C(133)—H(17) | 109.5 | H(42)—C(234)—H(43) | 109.5 |
C(134)—C(133)—C(131) | 109.1 (13) | H(42)—C(234)—C(233) | 110.8 |
H(16)—C(133)—H(17) | 109.5 | H(43)—C(234)—C(233) | 110.8 |
H(16)—C(133)—C(131) | 109.6 | H(44)—C(235)—H(45) | 109.5 |
H(17)—C(133)—C(131) | 109.5 | H(44)—C(235)—N(231) | 110.9 |
C(135)—C(134)—H(18) | 109.3 | H(44)—C(235)—C(234) | 111.0 |
C(135)—C(134)—H(19) | 109.4 | H(45)—C(235)—N(231) | 111.0 |
C(135)—C(134)—C(133) | 109.9 (14) | H(45)—C(235)—C(234) | 111.0 |
H(18)—C(134)—H(19) | 109.5 | N(231)—C(235)—C(234) | 103.3 (7) |
H(18)—C(134)—C(133) | 109.3 | H(46)—C(241)—H(47) | 109.5 |
H(19)—C(134)—C(133) | 109.5 | H(46)—C(241)—H(48) | 109.5 |
H(20)—C(135)—H(21) | 109.5 | H(46)—C(241)—O(241) | 109.5 |
H(20)—C(135)—N(131) | 110.5 | H(47)—C(241)—H(48) | 109.5 |
H(20)—C(135)—C(134) | 110.5 | H(47)—C(241)—O(241) | 109.4 |
H(21)—C(135)—N(131) | 110.7 | H(48)—C(241)—O(241) | 109.4 |
C(115)—O(111)—C(111)—C(112) | 71.0 (11) | H(11)—C(121)—C(123)—H(12) | 60.6 |
C(115)—O(111)—C(111)—C(113) | −54.1 (12) | H(11)—C(121)—C(123)—H(13) | −179.5 |
C(115)—O(111)—C(111)—C(114) | −169.8 (7) | H(11)—C(121)—C(123)—H(14) | −59.6 |
C(111)—O(111)—C(115)—O(112) | −10.1 (14) | N(131)—C(131)—C(132)—O(131) | −13.6 (14) |
C111—O111—C115—N121 | 168.1 (6) | N131—C131—C132—O141 | 168.7 (8) |
C(141)—O(141)—C(132)—O(131) | −2.3 (13) | C(133)—C(131)—C(132)—O(131) | 98.7 (11) |
C141—O141—C132—C131 | 175.4 (7) | C(133)—C(131)—C(132)—O(141) | −79.0 (9) |
C(132)—O(141)—C(141)—H(22) | −60.0 | H(15)—C(131)—C(132)—O(131) | −139.8 |
C(132)—O(141)—C(141)—H(23) | 60.0 | H(15)—C(131)—C(132)—O(141) | 42.5 |
C(132)—O(141)—C(141)—H(24) | 179.9 | N(131)—C(131)—C(133)—C(134) | −6.5 (14) |
C(215)—O(211)—C(211)—C(212) | 62.4 (10) | N(131)—C(131)—C(133)—H(16) | 113.6 |
C(215)—O(211)—C(211)—C(213) | −62.1 (10) | N(131)—C(131)—C(133)—H(17) | −126.4 |
C(215)—O(211)—C(211)—C(214) | −178.4 (7) | C(132)—C(131)—C(133)—C(134) | −127.3 (12) |
C(211)—O(211)—C(215)—O(212) | 1.7 (14) | C(132)—C(131)—C(133)—H(16) | −7.3 |
C211—O211—C215—N221 | −177.6 (7) | C(132)—C(131)—C(133)—H(17) | 112.8 |
C(241)—O(241)—C(232)—O(231) | −3.1 (12) | H(15)—C(131)—C(133)—C(134) | 111.2 |
C241—O241—C232—C231 | 172.6 (6) | H(15)—C(131)—C(133)—H(16) | −128.8 |
C(232)—O(241)—C(241)—H(46) | 179.8 | H(15)—C(131)—C(133)—H(17) | −8.8 |
C(232)—O(241)—C(241)—H(47) | −60.0 | C(131)—C(133)—C(134)—C(135) | 14.3 (17) |
C(232)—O(241)—C(241)—H(48) | 59.8 | C(131)—C(133)—C(134)—H(18) | 134.2 |
C121—N121—C115—O111 | −6.0 (13) | C(131)—C(133)—C(134)—H(19) | −105.9 |
C(121)—N(121)—C(115)—O(112) | 172.4 (8) | H(16)—C(133)—C(134)—C(135) | −105.7 |
H(10)—N(121)—C(115)—O(111) | 174.1 | H(16)—C(133)—C(134)—H(18) | 14.2 |
H(10)—N(121)—C(115)—O(112) | −7.6 | H(16)—C(133)—C(134)—H(19) | 134.2 |
C115—N121—C121—C122 | −60.4 (11) | H(17)—C(133)—C(134)—C(135) | 134.1 |
C(115)—N(121)—C(121)—C(123) | 179.6 (7) | H(17)—C(133)—C(134)—H(18) | −105.9 |
C(115)—N(121)—C(121)—H(11) | 60.4 | H(17)—C(133)—C(134)—H(19) | 14.0 |
H(10)—N(121)—C(121)—C(122) | 119.6 | C(133)—C(134)—C(135)—N(131) | −15.9 (16) |
H(10)—N(121)—C(121)—C(123) | −0.5 | C(133)—C(134)—C(135)—H(20) | −135.1 |
H(10)—N(121)—C(121)—H(11) | −119.6 | C(133)—C(134)—C(135)—H(21) | 103.5 |
C(131)—N(131)—C(122)—O(121) | −1.6 (13) | H(18)—C(134)—C(135)—N(131) | −135.9 |
C131—N131—C122—C121 | 173.0 (7) | H(18)—C(134)—C(135)—H(20) | 105.0 |
C(135)—N(131)—C(122)—O(121) | 174.3 (8) | H(18)—C(134)—C(135)—H(21) | −16.4 |
C(135)—N(131)—C(122)—C(121) | −11.1 (13) | H(19)—C(134)—C(135)—N(131) | 105.0 |
C122—N131—C131—C132 | −71.1 (11) | H(19)—C(134)—C(135)—H(20) | −14.9 |
C(122)—N(131)—C(131)—C(133) | 173.0 (9) | H(19)—C(134)—C(135)—H(21) | −135.9 |
C(122)—N(131)—C(131)—H(15) | 55.2 | O(211)—C(211)—C(212)—H(25) | −179.6 |
C(135)—N(131)—C(131)—C(132) | 112.4 (9) | O(211)—C(211)—C(212)—H(26) | −59.6 |
C(135)—N(131)—C(131)—C(133) | −3.5 (11) | O(211)—C(211)—C(212)—H(27) | 60.5 |
C(135)—N(131)—C(131)—H(15) | −121.3 | C(213)—C(211)—C(212)—H(25) | −56.0 |
C(122)—N(131)—C(135)—C(134) | −164.5 (10) | C(213)—C(211)—C(212)—H(26) | 64.0 |
C(122)—N(131)—C(135)—H(20) | −45.3 | C(213)—C(211)—C(212)—H(27) | −176.0 |
C(122)—N(131)—C(135)—H(21) | 76.1 | C(214)—C(211)—C(212)—H(25) | 67.8 |
C(131)—N(131)—C(135)—C(134) | 11.8 (12) | C(214)—C(211)—C(212)—H(26) | −172.2 |
C(131)—N(131)—C(135)—H(20) | 131.0 | C(214)—C(211)—C(212)—H(27) | −52.2 |
C(131)—N(131)—C(135)—H(21) | −107.6 | O(211)—C(211)—C(213)—H(28) | −51.7 |
C221—N221—C215—O211 | 176.3 (7) | O(211)—C(211)—C(213)—H(29) | 68.4 |
C(221)—N(221)—C(215)—O(212) | −3.0 (14) | O(211)—C(211)—C(213)—H(30) | −171.7 |
H(34)—N(221)—C(215)—O(211) | −3.6 | C(212)—C(211)—C(213)—H(28) | −175.1 |
H(34)—N(221)—C(215)—O(212) | 177.0 | C(212)—C(211)—C(213)—H(29) | −55.0 |
C215—N221—C221—C222 | −76.3 (11) | C(212)—C(211)—C(213)—H(30) | 65.0 |
C(215)—N(221)—C(221)—C(223) | 163.8 (8) | C(214)—C(211)—C(213)—H(28) | 59.7 |
C(215)—N(221)—C(221)—H(35) | 44.1 | C(214)—C(211)—C(213)—H(29) | 179.8 |
H(34)—N(221)—C(221)—C(222) | 103.6 | C(214)—C(211)—C(213)—H(30) | −60.3 |
H(34)—N(221)—C(221)—C(223) | −16.3 | O(211)—C(211)—C(214)—H(31) | −60.2 |
H(34)—N(221)—C(221)—H(35) | −136.0 | O(211)—C(211)—C(214)—H(32) | 59.8 |
C(231)—N(231)—C(222)—O(221) | −5.0 (12) | O(211)—C(211)—C(214)—H(33) | 179.9 |
C231—N231—C222—C221 | 172.0 (7) | C(212)—C(211)—C(214)—H(31) | 57.5 |
C(235)—N(231)—C(222)—O(221) | 167.2 (7) | C(212)—C(211)—C(214)—H(32) | 177.5 |
C(235)—N(231)—C(222)—C(221) | −15.8 (12) | C(212)—C(211)—C(214)—H(33) | −62.4 |
C222—N231—C231—C232 | −61.0 (9) | C(213)—C(211)—C(214)—H(31) | −177.2 |
C(222)—N(231)—C(231)—C(233) | 178.1 (6) | C(213)—C(211)—C(214)—H(32) | −57.2 |
C(222)—N(231)—C(231)—H(39) | 61.1 | C(213)—C(211)—C(214)—H(33) | 62.88 |
C(235)—N(231)—C(231)—C(232) | 125.8 (7) | N(221)—C(221)—C(222)—O(221) | −42.7 (11) |
C(235)—N(231)—C(231)—C(233) | 4.9 (8) | N221—C221—C222—N231 | 140.3 (8) |
C(235)—N(231)—C(231)—H(39) | −112.1 | C(223)—C(221)—C(222)—O(221) | 78.5 (10) |
C(222)—N(231)—C(235)—C(234) | −156.4 (7) | C(223)—C(221)—C(222)—N(231) | −98.6 (9) |
C(222)—N(231)—C(235)—H(44) | −37.3 | H(35)—C(221)—C(222)—O(221) | −163.1 |
C(222)—N(231)—C(235)—H(45) | 84.6 | H(35)—C(221)—C(222)—N(231) | 19.9 |
C(231)—N(231)—C(235)—C(234) | 16.4 (8) | N(221)—C(221)—C(223)—H(36) | 60.2 |
C(231)—N(231)—C(235)—H(44) | 135.4 | N(221)—C(221)—C(223)—H(37) | −179.9 |
C(231)—N(231)—C(235)—H(45) | −102.7 | N(221)—C(221)—C(223)—H(38) | −60.1 |
O(111)—C(111)—C(112)—H(1) | −180.0 | C(222)—C(221)—C(223)—H(36) | −61.7 |
O(111)—C(111)—C(112)—H(2) | −59.9 | C(222)—C(221)—C(223)—H(37) | 58.2 |
O(111)—C(111)—C(112)—H(3) | 60.1 | C(222)—C(221)—C(223)—H(38) | 178.0 |
C(113)—C(111)—C(112)—H(1) | −54.6 | H(35)—C(221)—C(223)—H(36) | 179.8 |
C(113)—C(111)—C(112)—H(2) | 65.5 | H(35)—C(221)—C(223)—H(37) | −60.3 |
C(113)—C(111)—C(112)—H(3) | −174.5 | H(35)—C(221)—C(223)—H(38) | 59.5 |
C(114)—C(111)—C(112)—H(1) | 67.5 | N(231)—C(231)—C(232)—O(231) | −30.9 (12) |
C(114)—C(111)—C(112)—H(2) | −172.4 | N231—C231—C232—O241 | 153.3 (7) |
C(114)—C(111)—C(112)—H(3) | −52.4 | C(233)—C(231)—C(232)—O(231) | 85.9 (11) |
O(111)—C(111)—C(113)—H(4) | −171.3 | C(233)—C(231)—C(232)—O(241) | −89.8 (8) |
O(111)—C(111)—C(113)—H(5) | −51.4 | H(39)—C(231)—C(232)—O(231) | −153.0 |
O(111)—C(111)—C(113)—H(6) | 68.7 | H(39)—C(231)—C(232)—O(241) | 31.4 |
C(112)—C(111)—C(113)—H(4) | 64.4 | N(231)—C(231)—C(233)—C(234) | −24.0 (8) |
C(112)—C(111)—C(113)—H(5) | −175.7 | N(231)—C(231)—C(233)—H(40) | 95.1 |
C(112)—C(111)—C(113)—H(6) | −55.6 | N(231)—C(231)—C(233)—H(41) | −143.0 |
C(114)—C(111)—C(113)—H(4) | −59.8 | C(232)—C(231)—C(233)—C(234) | −145.9 (7) |
C(114)—C(111)—C(113)—H(5) | 59.8 | C(232)—C(231)—C(233)—H(40) | −26.8 |
C(114)—C(111)—C(113)—H(6) | −179.8 | C(232)—C(231)—C(233)—H(41) | 95.1 |
O(111)—C(111)—C(114)—H(7) | −59.9 | H(39)—C(231)—C(233)—C(234) | 93.0 |
O(111)—C(111)—C(114)—H(8) | 60.1 | H(39)—C(231)—C(233)—H(40) | −147.9 |
O(111)—C(111)—C(114)—H(9) | −179.8 | H(39)—C(231)—C(233)—H(41) | −26.0 |
C(112)—C(111)—C(114)—H(7) | 57.8 | C(231)—C(233)—C(234)—C(235) | 34.2 (9) |
C(112)—C(111)—C(114)—H(8) | 177.9 | C(231)—C(233)—C(234)—H(42) | 153.3 |
C(112)—C(111)—C(114)—H(9) | −62.0 | C(231)—C(233)—C(234)—H(43) | −85.0 |
C(113)—C(111)—C(114)—H(7) | −178.4 | H(40)—C(233)—C(234)—C(235) | −84.9 |
C(113)—C(111)—C(114)—H(8) | −58.3 | H(40)—C(233)—C(234)—H(42) | 34.2 |
C(113)—C(111)—C(114)—H(9) | 61.8 | H(40)—C(233)—C(234)—H(43) | 155.9 |
N(121)—C(121)—C(122)—O(121) | −32.4 (11) | H(41)—C(233)—C(234)—C(235) | 153.2 |
N121—C121—C122—N131 | 153.2 (8) | H(41)—C(233)—C(234)—H(42) | −87.6 |
C(123)—C(121)—C(122)—O(121) | 87.3 (10) | H(41)—C(233)—C(234)—H(43) | 34.1 |
C(123)—C(121)—C(122)—N(131) | −87.2 (9) | C(233)—C(234)—C(235)—N(231) | −30.8 (9) |
H(11)—C(121)—C(122)—O(121) | −153.3 | C(233)—C(234)—C(235)—H(44) | −149.7 |
H(11)—C(121)—C(122)—N(131) | 32.3 | C(233)—C(234)—C(235)—H(45) | 88.3 |
N(121)—C(121)—C(123)—H(12) | −58.6 | H(42)—C(234)—C(235)—N(231) | −149.9 |
N(121)—C(121)—C(123)—H(13) | 61.3 | H(42)—C(234)—C(235)—H(44) | 91.1 |
N(121)—C(121)—C(123)—H(14) | −178.7 | H(42)—C(234)—C(235)—H(45) | −30.5 |
C(122)—C(121)—C(123)—H(12) | 180.0 | H(43)—C(234)—C(235)—N(231) | 88.5 |
C(122)—C(121)—C(123)—H(13) | −60.1 | H(43)—C(234)—C(235)—H(44) | −30.5 |
C(122)—C(121)—C(123)—H(14) | 59.8 | H(43)—C(234)—C(235)—H(45) | −152.4 |
D—H···A | D—H | H···A | D···A | D—H···A |
N121—H10···O221 | 0.95 | 1.86 | 2.794 (12) | 168 |
N221—H34···O112 | 0.95 | 2.21 | 3.070 (11) | 150 |