The title compound, C
12H
18N
2O
3, was synthesized in 87.2% yield by condensation of
L-leucine methyl ester with 2-trichloroacetylpyrrole at room temperature. There are two chemically equivalent and crystallographically independent molecules in the asymmetric unit. In the crystal structure, intermolecular N—H
O hydrogen-bonding interactions link the molecules into extended chains parallel to the
c axis.
Supporting information
CCDC reference: 289622
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.120
- Data-to-parameter ratio = 10.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT707_ALERT_1_A D...A Calc 16.242(9), Rep 3.054(3), Dev.. 1465.33 Sigma
N3 -O2 1.555 2.564
PLAT726_ALERT_1_A H...A Calc 17.05000, Rep 2.347(3) Dev... 14.70 Ang.
H3 -O2 1.555 2.564
PLAT728_ALERT_1_A D-H..A Calc 20.00, Rep 139.8(3) Dev... 119.80 Deg.
N3 -H3 -O2 1.555 1.555 2.564
Alert level B
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C20
Alert level C
STRVA01_ALERT_4_C Flack test results are meaningless.
From the CIF: _refine_ls_abs_structure_Flack 0.000
From the CIF: _refine_ls_abs_structure_Flack_su 10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 2688.00 Ang-3
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.66 Ratio
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.27 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.12 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.81 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT737_ALERT_1_C D...A Calc 16.242(9), Rep 3.054(3) ...... 3.00 su-Rat
N3 -O2 1.555 2.564
PLAT756_ALERT_4_C H...A Calc 2.23000, Rep 2.228(3) ...... Senseless su
H1 -O5 1.555 1.555
PLAT756_ALERT_4_C H...A Calc 2.14000, Rep 2.139(3) ...... Senseless su
H2 -O4 1.555 2.564
PLAT756_ALERT_4_C H...A Calc 17.05000, Rep 2.347(3) ...... Senseless su
H3 -O2 1.555 2.564
PLAT756_ALERT_4_C H...A Calc 2.04000, Rep 2.045(3) ...... Senseless su
H4 -O1 1.555 1.555
PLAT758_ALERT_4_C D-H..A Calc 170.00, Rep 169.8(3) ...... Senseless su
N1 -H1 -O5 1.555 1.555 1.555
PLAT758_ALERT_4_C D-H..A Calc 158.00, Rep 158.1(3) ...... Senseless su
N4 -H4 -O1 1.555 1.555 1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
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 27.06
From the CIF: _reflns_number_total 3301
Count of symmetry unique reflns 3331
Completeness (_total/calc) 99.10%
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
3 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
20 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
10 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(
S)-Methyl 4-methyl-2-(1
H-pyrrole-2-carboxamido)pentanoate
top
Crystal data top
C12H18N2O3 | Dx = 1.178 Mg m−3 |
Mr = 238.28 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 941 reflections |
a = 8.920 (4) Å | θ = 2.5–21.9° |
b = 16.282 (8) Å | µ = 0.09 mm−1 |
c = 18.504 (9) Å | T = 298 K |
V = 2688 (2) Å3 | Block, colorless |
Z = 8 | 0.50 × 0.26 × 0.18 mm |
F(000) = 1024 | |
Data collection top
Bruker SMART 1K CCD area-detector diffractometer | 3301 independent reflections |
Radiation source: fine-focus sealed tube | 2196 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 27.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→10 |
Tmin = 0.974, Tmax = 0.985 | k = −18→20 |
14949 measured reflections | l = −21→23 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0622P)2 + 0.3014P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3301 reflections | Δρmax = 0.17 e Å−3 |
314 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
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 | |
O1 | 0.3778 (2) | 0.57496 (13) | 0.58826 (9) | 0.0624 (5) | |
O2 | 0.5896 (3) | 0.54643 (14) | 0.43995 (13) | 0.0750 (6) | |
O3 | 0.7049 (2) | 0.46445 (16) | 0.51887 (17) | 0.0944 (9) | |
O4 | 0.3196 (3) | 0.55723 (12) | 0.85733 (10) | 0.0679 (6) | |
O5 | 0.2675 (3) | 0.73630 (14) | 0.70795 (13) | 0.0776 (6) | |
O6 | 0.4381 (3) | 0.79811 (12) | 0.77676 (16) | 0.0906 (8) | |
N1 | 0.1518 (3) | 0.68715 (15) | 0.55732 (15) | 0.0660 (7) | |
H1 | 0.1879 | 0.6944 | 0.5999 | 0.079* | |
N2 | 0.3164 (2) | 0.49524 (14) | 0.49418 (12) | 0.0509 (6) | |
H2 | 0.2504 | 0.4818 | 0.4624 | 0.061* | |
N3 | 0.1223 (3) | 0.43291 (14) | 0.81157 (13) | 0.0643 (7) | |
H3 | 0.1074 | 0.4453 | 0.8562 | 0.077* | |
N4 | 0.3861 (3) | 0.58430 (13) | 0.74260 (11) | 0.0521 (6) | |
H4 | 0.3844 | 0.5676 | 0.6985 | 0.063* | |
C1 | 0.1866 (3) | 0.62314 (16) | 0.51233 (14) | 0.0508 (6) | |
C2 | 0.1076 (4) | 0.63459 (19) | 0.45032 (16) | 0.0637 (8) | |
H2A | 0.1099 | 0.6008 | 0.4098 | 0.076* | |
C3 | 0.0224 (4) | 0.7061 (2) | 0.4580 (2) | 0.0818 (10) | |
H3A | −0.0426 | 0.7284 | 0.4240 | 0.098* | |
C4 | 0.0525 (4) | 0.7368 (2) | 0.5245 (2) | 0.0845 (11) | |
H4A | 0.0114 | 0.7843 | 0.5441 | 0.101* | |
C5 | 0.2983 (3) | 0.56371 (16) | 0.53443 (13) | 0.0477 (6) | |
C6 | 0.4475 (3) | 0.44499 (16) | 0.50510 (15) | 0.0514 (6) | |
H6 | 0.4541 | 0.4302 | 0.5564 | 0.062* | |
C7 | 0.4417 (3) | 0.36659 (16) | 0.46033 (15) | 0.0562 (7) | |
H7A | 0.5386 | 0.3398 | 0.4637 | 0.067* | |
H7B | 0.4266 | 0.3817 | 0.4101 | 0.067* | |
C8 | 0.3211 (3) | 0.30440 (17) | 0.48120 (16) | 0.0602 (8) | |
H8 | 0.2238 | 0.3323 | 0.4818 | 0.072* | |
C9 | 0.3155 (5) | 0.2362 (2) | 0.4257 (2) | 0.0909 (12) | |
H9A | 0.4094 | 0.2074 | 0.4254 | 0.136* | |
H9B | 0.2973 | 0.2592 | 0.3787 | 0.136* | |
H9C | 0.2363 | 0.1987 | 0.4378 | 0.136* | |
C10 | 0.3496 (5) | 0.2682 (3) | 0.5553 (2) | 0.0939 (12) | |
H10A | 0.4485 | 0.2450 | 0.5568 | 0.141* | |
H10B | 0.2771 | 0.2260 | 0.5649 | 0.141* | |
H10C | 0.3412 | 0.3105 | 0.5912 | 0.141* | |
C11 | 0.5869 (3) | 0.49241 (19) | 0.48417 (18) | 0.0605 (8) | |
C12 | 0.8494 (4) | 0.5019 (3) | 0.4993 (3) | 0.1268 (19) | |
H12A | 0.8783 | 0.4839 | 0.4519 | 0.190* | |
H12B | 0.9243 | 0.4856 | 0.5337 | 0.190* | |
H12C | 0.8398 | 0.5606 | 0.4996 | 0.190* | |
C13 | 0.2198 (3) | 0.47288 (16) | 0.76628 (14) | 0.0512 (7) | |
C14 | 0.2100 (4) | 0.4341 (2) | 0.70168 (18) | 0.0769 (9) | |
H14 | 0.2634 | 0.4474 | 0.6602 | 0.092* | |
C15 | 0.1061 (5) | 0.3708 (2) | 0.7082 (2) | 0.0913 (11) | |
H15 | 0.0781 | 0.3344 | 0.6719 | 0.110* | |
C16 | 0.0535 (4) | 0.3715 (2) | 0.7759 (2) | 0.0785 (10) | |
H16 | −0.0178 | 0.3358 | 0.7950 | 0.094* | |
C17 | 0.3105 (3) | 0.54096 (15) | 0.79258 (14) | 0.0480 (6) | |
C18 | 0.4704 (3) | 0.65785 (15) | 0.75956 (15) | 0.0513 (7) | |
H18 | 0.4957 | 0.6570 | 0.8111 | 0.062* | |
C19 | 0.6155 (3) | 0.66454 (17) | 0.71609 (17) | 0.0612 (7) | |
H19A | 0.5897 | 0.6665 | 0.6652 | 0.073* | |
H19B | 0.6632 | 0.7163 | 0.7281 | 0.073* | |
C20 | 0.7287 (4) | 0.5965 (2) | 0.7271 (2) | 0.0742 (9) | |
H20 | 0.6838 | 0.5451 | 0.7100 | 0.089* | |
C21 | 0.8666 (5) | 0.6139 (4) | 0.6809 (3) | 0.150 (2) | |
H21A | 0.9237 | 0.6575 | 0.7024 | 0.225* | |
H21B | 0.8356 | 0.6299 | 0.6332 | 0.225* | |
H21C | 0.9273 | 0.5654 | 0.6779 | 0.225* | |
C22 | 0.7721 (7) | 0.5851 (4) | 0.8033 (2) | 0.157 (3) | |
H22A | 0.8407 | 0.5398 | 0.8071 | 0.236* | |
H22B | 0.6844 | 0.5738 | 0.8317 | 0.236* | |
H22C | 0.8195 | 0.6341 | 0.8208 | 0.236* | |
C23 | 0.3784 (4) | 0.73326 (16) | 0.74453 (15) | 0.0570 (7) | |
C24 | 0.3699 (5) | 0.8775 (2) | 0.7626 (3) | 0.1181 (17) | |
H24A | 0.3500 | 0.8828 | 0.7119 | 0.177* | |
H24B | 0.4370 | 0.9204 | 0.7777 | 0.177* | |
H24C | 0.2776 | 0.8819 | 0.7890 | 0.177* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0667 (12) | 0.0752 (12) | 0.0451 (10) | 0.0026 (12) | −0.0039 (10) | −0.0101 (10) |
O2 | 0.0781 (15) | 0.0708 (13) | 0.0760 (14) | −0.0155 (12) | 0.0070 (13) | 0.0101 (12) |
O3 | 0.0529 (13) | 0.0861 (16) | 0.144 (2) | −0.0094 (12) | −0.0202 (15) | 0.0242 (16) |
O4 | 0.0894 (15) | 0.0703 (13) | 0.0441 (11) | −0.0217 (13) | 0.0078 (10) | 0.0002 (9) |
O5 | 0.0761 (15) | 0.0736 (14) | 0.0831 (15) | 0.0146 (12) | −0.0180 (13) | −0.0089 (12) |
O6 | 0.0783 (16) | 0.0481 (11) | 0.145 (2) | −0.0027 (12) | −0.0233 (16) | −0.0101 (14) |
N1 | 0.0682 (16) | 0.0603 (14) | 0.0695 (16) | 0.0046 (14) | 0.0030 (13) | −0.0091 (13) |
N2 | 0.0506 (13) | 0.0531 (13) | 0.0491 (13) | 0.0015 (11) | −0.0074 (10) | −0.0060 (11) |
N3 | 0.0674 (15) | 0.0610 (14) | 0.0646 (15) | −0.0159 (14) | 0.0010 (13) | 0.0045 (12) |
N4 | 0.0676 (15) | 0.0489 (12) | 0.0399 (11) | −0.0092 (12) | 0.0010 (11) | −0.0016 (10) |
C1 | 0.0511 (15) | 0.0477 (14) | 0.0536 (16) | −0.0046 (13) | 0.0095 (13) | 0.0000 (12) |
C2 | 0.0641 (19) | 0.0695 (19) | 0.0574 (17) | 0.0049 (16) | 0.0001 (15) | 0.0059 (15) |
C3 | 0.079 (2) | 0.083 (2) | 0.083 (2) | 0.021 (2) | 0.0016 (19) | 0.021 (2) |
C4 | 0.088 (2) | 0.0621 (19) | 0.104 (3) | 0.020 (2) | 0.015 (2) | 0.007 (2) |
C5 | 0.0487 (14) | 0.0530 (15) | 0.0415 (13) | −0.0058 (13) | 0.0049 (12) | 0.0011 (12) |
C6 | 0.0510 (15) | 0.0529 (15) | 0.0502 (15) | 0.0002 (13) | 0.0010 (12) | 0.0021 (12) |
C7 | 0.0526 (16) | 0.0570 (15) | 0.0590 (16) | 0.0028 (14) | 0.0085 (14) | −0.0002 (14) |
C8 | 0.0547 (16) | 0.0540 (16) | 0.0720 (19) | −0.0023 (14) | 0.0055 (15) | −0.0003 (15) |
C9 | 0.112 (3) | 0.070 (2) | 0.091 (3) | −0.024 (2) | 0.009 (2) | −0.016 (2) |
C10 | 0.109 (3) | 0.091 (3) | 0.082 (2) | −0.033 (2) | 0.004 (2) | 0.014 (2) |
C11 | 0.0537 (17) | 0.0548 (17) | 0.073 (2) | −0.0023 (14) | −0.0029 (15) | −0.0039 (16) |
C12 | 0.054 (2) | 0.138 (4) | 0.188 (5) | −0.032 (3) | −0.006 (3) | −0.006 (4) |
C13 | 0.0530 (16) | 0.0498 (14) | 0.0507 (16) | −0.0019 (13) | 0.0007 (13) | 0.0042 (12) |
C14 | 0.078 (2) | 0.084 (2) | 0.069 (2) | −0.029 (2) | 0.0095 (18) | −0.0122 (18) |
C15 | 0.099 (3) | 0.090 (2) | 0.085 (3) | −0.034 (2) | −0.003 (2) | −0.024 (2) |
C16 | 0.071 (2) | 0.0688 (19) | 0.096 (3) | −0.0276 (19) | −0.001 (2) | 0.0043 (19) |
C17 | 0.0515 (15) | 0.0455 (13) | 0.0469 (15) | 0.0029 (12) | 0.0021 (13) | 0.0031 (12) |
C18 | 0.0602 (17) | 0.0473 (14) | 0.0465 (14) | −0.0081 (14) | −0.0023 (13) | 0.0006 (12) |
C19 | 0.0612 (17) | 0.0576 (16) | 0.0648 (17) | −0.0035 (15) | −0.0009 (15) | 0.0091 (14) |
C20 | 0.068 (2) | 0.0604 (19) | 0.094 (2) | −0.0003 (17) | −0.0008 (19) | −0.0073 (18) |
C21 | 0.088 (3) | 0.174 (5) | 0.188 (6) | 0.031 (4) | 0.046 (4) | 0.004 (5) |
C22 | 0.160 (5) | 0.200 (6) | 0.111 (4) | 0.104 (5) | −0.056 (4) | −0.003 (4) |
C23 | 0.0569 (17) | 0.0518 (16) | 0.0623 (17) | −0.0050 (15) | 0.0028 (15) | −0.0001 (14) |
C24 | 0.105 (3) | 0.0450 (17) | 0.204 (5) | 0.009 (2) | −0.010 (4) | −0.009 (3) |
Geometric parameters (Å, º) top
O1—C5 | 1.236 (3) | C8—H8 | 0.9800 |
O2—C11 | 1.202 (4) | C9—H9A | 0.9600 |
O3—C11 | 1.314 (4) | C9—H9B | 0.9600 |
O3—C12 | 1.471 (4) | C9—H9C | 0.9600 |
O4—C17 | 1.230 (3) | C10—H10A | 0.9600 |
O5—C23 | 1.200 (4) | C10—H10B | 0.9600 |
O6—C23 | 1.324 (3) | C10—H10C | 0.9600 |
O6—C24 | 1.453 (4) | C12—H12A | 0.9600 |
N1—C4 | 1.345 (4) | C12—H12B | 0.9600 |
N1—C1 | 1.369 (4) | C12—H12C | 0.9600 |
N1—H1 | 0.8600 | C13—C14 | 1.355 (4) |
N2—C5 | 1.350 (3) | C13—C17 | 1.456 (4) |
N2—C6 | 1.442 (3) | C14—C15 | 1.391 (5) |
N2—H2 | 0.8600 | C14—H14 | 0.9300 |
N3—C16 | 1.346 (4) | C15—C16 | 1.338 (5) |
N3—C13 | 1.372 (4) | C15—H15 | 0.9300 |
N3—H3 | 0.8600 | C16—H16 | 0.9300 |
N4—C17 | 1.345 (3) | C18—C23 | 1.503 (4) |
N4—C18 | 1.448 (3) | C18—C19 | 1.528 (4) |
N4—H4 | 0.8600 | C18—H18 | 0.9800 |
C1—C2 | 1.359 (4) | C19—C20 | 1.513 (4) |
C1—C5 | 1.448 (4) | C19—H19A | 0.9700 |
C2—C3 | 1.398 (5) | C19—H19B | 0.9700 |
C2—H2A | 0.9300 | C20—C22 | 1.474 (5) |
C3—C4 | 1.355 (5) | C20—C21 | 1.525 (6) |
C3—H3A | 0.9300 | C20—H20 | 0.9800 |
C4—H4A | 0.9300 | C21—H21A | 0.9600 |
C6—C11 | 1.514 (4) | C21—H21B | 0.9600 |
C6—C7 | 1.523 (4) | C21—H21C | 0.9600 |
C6—H6 | 0.9800 | C22—H22A | 0.9600 |
C7—C8 | 1.527 (4) | C22—H22B | 0.9600 |
C7—H7A | 0.9700 | C22—H22C | 0.9600 |
C7—H7B | 0.9700 | C24—H24A | 0.9600 |
C8—C10 | 1.514 (5) | C24—H24B | 0.9600 |
C8—C9 | 1.514 (4) | C24—H24C | 0.9600 |
| | | |
C11—O3—C12 | 116.0 (3) | O3—C11—C6 | 110.9 (3) |
C23—O6—C24 | 117.4 (3) | O3—C12—H12A | 109.5 |
C4—N1—C1 | 109.4 (3) | O3—C12—H12B | 109.5 |
C4—N1—H1 | 125.3 | H12A—C12—H12B | 109.5 |
C1—N1—H1 | 125.3 | O3—C12—H12C | 109.5 |
C5—N2—C6 | 119.2 (2) | H12A—C12—H12C | 109.5 |
C5—N2—H2 | 120.4 | H12B—C12—H12C | 109.5 |
C6—N2—H2 | 120.4 | C14—C13—N3 | 106.1 (3) |
C16—N3—C13 | 110.0 (3) | C14—C13—C17 | 133.3 (3) |
C16—N3—H3 | 125.0 | N3—C13—C17 | 120.6 (2) |
C13—N3—H3 | 125.0 | C13—C14—C15 | 108.2 (3) |
C17—N4—C18 | 123.1 (2) | C13—C14—H14 | 125.9 |
C17—N4—H4 | 118.5 | C15—C14—H14 | 125.9 |
C18—N4—H4 | 118.5 | C16—C15—C14 | 108.0 (3) |
C2—C1—N1 | 107.0 (3) | C16—C15—H15 | 126.0 |
C2—C1—C5 | 133.4 (3) | C14—C15—H15 | 126.0 |
N1—C1—C5 | 119.5 (3) | C15—C16—N3 | 107.8 (3) |
C1—C2—C3 | 108.0 (3) | C15—C16—H16 | 126.1 |
C1—C2—H2A | 126.0 | N3—C16—H16 | 126.1 |
C3—C2—H2A | 126.0 | O4—C17—N4 | 121.6 (3) |
C4—C3—C2 | 107.0 (3) | O4—C17—C13 | 121.7 (2) |
C4—C3—H3A | 126.5 | N4—C17—C13 | 116.6 (2) |
C2—C3—H3A | 126.5 | N4—C18—C23 | 110.6 (2) |
N1—C4—C3 | 108.6 (3) | N4—C18—C19 | 112.6 (2) |
N1—C4—H4A | 125.7 | C23—C18—C19 | 107.9 (2) |
C3—C4—H4A | 125.7 | N4—C18—H18 | 108.5 |
O1—C5—N2 | 119.9 (3) | C23—C18—H18 | 108.5 |
O1—C5—C1 | 121.6 (2) | C19—C18—H18 | 108.5 |
N2—C5—C1 | 118.5 (2) | C20—C19—C18 | 116.2 (2) |
N2—C6—C11 | 109.9 (2) | C20—C19—H19A | 108.2 |
N2—C6—C7 | 111.8 (2) | C18—C19—H19A | 108.2 |
C11—C6—C7 | 108.4 (2) | C20—C19—H19B | 108.2 |
N2—C6—H6 | 108.9 | C18—C19—H19B | 108.2 |
C11—C6—H6 | 108.9 | H19A—C19—H19B | 107.4 |
C7—C6—H6 | 108.9 | C22—C20—C19 | 113.4 (3) |
C6—C7—C8 | 116.3 (2) | C22—C20—C21 | 110.4 (4) |
C6—C7—H7A | 108.2 | C19—C20—C21 | 109.0 (3) |
C8—C7—H7A | 108.2 | C22—C20—H20 | 108.0 |
C6—C7—H7B | 108.2 | C19—C20—H20 | 108.0 |
C8—C7—H7B | 108.2 | C21—C20—H20 | 108.0 |
H7A—C7—H7B | 107.4 | C20—C21—H21A | 109.5 |
C10—C8—C9 | 109.5 (3) | C20—C21—H21B | 109.5 |
C10—C8—C7 | 111.7 (3) | H21A—C21—H21B | 109.5 |
C9—C8—C7 | 109.8 (3) | C20—C21—H21C | 109.5 |
C10—C8—H8 | 108.6 | H21A—C21—H21C | 109.5 |
C9—C8—H8 | 108.6 | H21B—C21—H21C | 109.5 |
C7—C8—H8 | 108.6 | C20—C22—H22A | 109.5 |
C8—C9—H9A | 109.5 | C20—C22—H22B | 109.5 |
C8—C9—H9B | 109.5 | H22A—C22—H22B | 109.5 |
H9A—C9—H9B | 109.5 | C20—C22—H22C | 109.5 |
C8—C9—H9C | 109.5 | H22A—C22—H22C | 109.5 |
H9A—C9—H9C | 109.5 | H22B—C22—H22C | 109.5 |
H9B—C9—H9C | 109.5 | O5—C23—O6 | 123.6 (3) |
C8—C10—H10A | 109.5 | O5—C23—C18 | 126.0 (3) |
C8—C10—H10B | 109.5 | O6—C23—C18 | 110.4 (3) |
H10A—C10—H10B | 109.5 | O6—C24—H24A | 109.5 |
C8—C10—H10C | 109.5 | O6—C24—H24B | 109.5 |
H10A—C10—H10C | 109.5 | H24A—C24—H24B | 109.5 |
H10B—C10—H10C | 109.5 | O6—C24—H24C | 109.5 |
O2—C11—O3 | 124.8 (3) | H24A—C24—H24C | 109.5 |
O2—C11—C6 | 124.3 (3) | H24B—C24—H24C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5 | 0.86 | 2.23 (1) | 3.078 (3) | 170 (1) |
N2—H2···O4i | 0.86 | 2.14 (1) | 2.935 (3) | 154 (1) |
N3—H3···O2i | 0.86 | 2.35 (1) | 3.054 (3) | 140 (1) |
N4—H4···O1 | 0.86 | 2.05 (1) | 2.861 (3) | 158 (1) |
Symmetry code: (i) −x+1/2, −y+1, z−1/2. |