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The crystal structure of 2-methyl-2-phenyl-1,3-propanediol dicarbamate (methylfelbamate), C
12H
16N
2O
4, contains two independent molecules in the asymmetric unit. The hydrogen-bonding scheme is three-dimensional and involves interactions of the type N—H
O, C—H
O and N—H
(π-arene). Stereochemical and molecular modelling investigations indicate that the mechanism for anti-epileptic action of the compound is probably different from those of other anticonvulsants.
Supporting information
CCDC reference: 272023
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.006 Å
- R factor = 0.045
- wR factor = 0.111
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level A
THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550
Calculated sin(theta_max)/wavelength = 0.5313
| Author Response: ...'see _exptl_special_details'
|
PLAT023_ALERT_3_A Resolution (too) Low [sin(th)/Lambda < 0.6]..... 55.00 Deg.
| Author Response: ...'see _exptl_special_details'
|
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 55.00 Deg.
| Author Response: ...'see _exptl_special_details'
|
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.04 Ratio
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C5A
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C1A
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist. C1A -C6A 1.36 Ang.
Alert level C
REFNR01_ALERT_3_C Ratio of reflections to parameters is < 10 for a
centrosymmetric structure
sine(theta)/lambda 0.5313
Proportion of unique data used 1.0000
Ratio reflections to parameters 9.3508
PLAT088_ALERT_3_C Poor Data / Parameter Ratio .................... 9.35
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11A
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11B
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.12
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
PLAT420_ALERT_2_C D-H Without Acceptor N2A - H103 ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N2B - H204 ... ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 8
3 ALERT level A = In general: serious problem
4 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
11 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: Picker Operating Manual (Picker, 1967); cell refinement: Picker Operating Manual; data reduction: Picker Operating Manual; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
2-Methyl-2-phenyl-1,3-propanediol dicarbamate
top
Crystal data top
C12H16N2O4 | Z = 4 |
Mr = 252.27 | F(000) = 536 |
Triclinic, P1 | Dx = 1.245 Mg m−3 |
a = 9.984 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 12.040 (3) Å | Cell parameters from 16 reflections |
c = 14.360 (4) Å | θ = 22–50° |
α = 96.74 (2)° | µ = 0.79 mm−1 |
β = 95.82 (2)° | T = 294 K |
γ = 126.51 (3)° | Needle, colourless |
V = 1345.8 (8) Å3 | 0.5 × 0.2 × 0.2 mm |
Data collection top
Picker FACS-1 four-circle diffractometer | Rint = 0.017 |
Radiation source: fine-focus sealed tube | θmax = 55.0°, θmin = 3.2° |
Ni-filtered radiation monochromator | h = 0→10 |
θ/2θ scans | k = −12→10 |
3626 measured reflections | l = −15→15 |
3385 independent reflections | 3 standard reflections every 100 reflections |
2591 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.4196P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3385 reflections | Δρmax = 0.14 e Å−3 |
362 parameters | Δρmin = −0.13 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0068 (5) |
Special details top
Experimental. There were no observable reflections above θ = 55°, only the background noise.
High temperature factors for outer phenyl ring atoms are commented in the
comment section. The data were collected on a crystal with dimensions 0.45
x 0.15 x. 10 mm mounted along its long axis. |
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 | |
C1A | 0.5149 (3) | 0.9835 (3) | 0.23702 (18) | 0.0472 (7) | |
C2A | 0.5844 (4) | 0.9179 (4) | 0.2572 (3) | 0.0799 (10) | |
H2A | 0.5585 | 0.8726 | 0.3082 | 0.132 (5)* | |
C3A | 0.6925 (5) | 0.9163 (5) | 0.2044 (4) | 0.1169 (16) | |
H3A | 0.7368 | 0.8699 | 0.2204 | 0.132 (5)* | |
C4A | 0.7329 (6) | 0.9797 (6) | 0.1319 (4) | 0.1343 (19) | |
H4A | 0.8045 | 0.9779 | 0.0962 | 0.132 (5)* | |
C5A | 0.6684 (7) | 1.0471 (7) | 0.1106 (4) | 0.168 (3) | |
H5A | 0.6986 | 1.0946 | 0.0608 | 0.132 (5)* | |
C6A | 0.5581 (5) | 1.0471 (5) | 0.1614 (3) | 0.1156 (16) | |
H6A | 0.5123 | 1.0918 | 0.1435 | 0.132 (5)* | |
C7A | 0.3992 (3) | 0.9867 (2) | 0.29713 (16) | 0.0416 (6) | |
C8A | 0.2945 (3) | 1.0244 (2) | 0.24649 (16) | 0.0447 (6) | |
H8A1 | 0.2296 | 1.0322 | 0.2891 | 0.067 (2)* | |
H8A2 | 0.3697 | 1.1150 | 0.2293 | 0.067 (2)* | |
C9A | 0.5083 (3) | 1.1022 (3) | 0.38978 (19) | 0.0585 (8) | |
H9A1 | 0.4351 | 1.0995 | 0.4305 | 0.067 (2)* | |
H9A2 | 0.5813 | 1.0858 | 0.4246 | 0.067 (2)* | |
C10A | 0.1020 (3) | 0.9488 (3) | 0.10240 (17) | 0.0417 (6) | |
C11A | 0.7723 (3) | 1.3340 (3) | 0.41496 (18) | 0.0504 (7) | |
C12A | 0.2810 (3) | 0.8479 (3) | 0.32800 (19) | 0.0519 (7) | |
H12A | 0.2153 | 0.7712 | 0.2723 | 0.067 (2)* | |
H12B | 0.2056 | 0.8523 | 0.3618 | 0.067 (2)* | |
H12C | 0.3477 | 0.8325 | 0.3693 | 0.067 (2)* | |
O1A | 0.1799 (2) | 0.91556 (16) | 0.16110 (11) | 0.0468 (5) | |
O2A | 0.1268 (2) | 1.06209 (19) | 0.11842 (12) | 0.0592 (5) | |
O3A | 0.6111 (2) | 1.23877 (18) | 0.36534 (14) | 0.0727 (6) | |
O4A | 0.8342 (2) | 1.30945 (18) | 0.47864 (13) | 0.0594 (5) | |
N1A | −0.0057 (3) | 0.8450 (3) | 0.02634 (18) | 0.0609 (7) | |
H101 | −0.045 (3) | 0.867 (3) | −0.017 (2) | 0.056 (8)* | |
H102 | −0.010 (3) | 0.774 (3) | 0.0180 (19) | 0.055 (9)* | |
N2A | 0.8478 (4) | 1.4540 (3) | 0.3871 (2) | 0.0821 (10) | |
H103 | 0.793 (4) | 1.465 (4) | 0.339 (3) | 0.098 (12)* | |
H104 | 0.946 (4) | 1.526 (4) | 0.419 (2) | 0.085 (11)* | |
C1B | 0.4971 (3) | 0.4980 (3) | 0.26383 (19) | 0.0516 (7) | |
C2B | 0.6577 (4) | 0.6249 (3) | 0.3006 (3) | 0.0754 (10) | |
H2B | 0.6752 | 0.6862 | 0.3548 | 0.132 (5)* | |
C3B | 0.7931 (5) | 0.6619 (5) | 0.2576 (4) | 0.1065 (15) | |
H3B | 0.8996 | 0.7487 | 0.2829 | 0.132 (5)* | |
C4B | 0.7742 (7) | 0.5753 (7) | 0.1803 (5) | 0.1212 (18) | |
H4B | 0.8665 | 0.6018 | 0.1526 | 0.132 (5)* | |
C5B | 0.6180 (6) | 0.4481 (5) | 0.1431 (3) | 0.1106 (14) | |
H5B | 0.6038 | 0.3871 | 0.0899 | 0.132 (5)* | |
C6B | 0.4797 (4) | 0.4093 (4) | 0.1842 (2) | 0.0794 (10) | |
H6B | 0.3738 | 0.3224 | 0.1579 | 0.132 (5)* | |
C7B | 0.3437 (3) | 0.4531 (2) | 0.30873 (16) | 0.0451 (6) | |
C8B | 0.2885 (3) | 0.3191 (3) | 0.34336 (18) | 0.0488 (7) | |
H8B1 | 0.2513 | 0.2438 | 0.2891 | 0.067 (2)* | |
H8B2 | 0.3837 | 0.3376 | 0.3871 | 0.067 (2)* | |
C9B | 0.1962 (3) | 0.4145 (3) | 0.23310 (19) | 0.0541 (7) | |
H9B1 | 0.1614 | 0.3358 | 0.1826 | 0.067 (2)* | |
H9B2 | 0.0994 | 0.3865 | 0.2617 | 0.067 (2)* | |
C10B | 0.0965 (4) | 0.1674 (3) | 0.43385 (18) | 0.0482 (7) | |
C11B | 0.1554 (4) | 0.5157 (3) | 0.11300 (18) | 0.0521 (7) | |
C12B | 0.3844 (4) | 0.5665 (3) | 0.3921 (2) | 0.0685 (9) | |
H12D | 0.4732 | 0.5873 | 0.4417 | 0.067 (2)* | |
H12E | 0.2841 | 0.5328 | 0.4171 | 0.067 (2)* | |
H12F | 0.4217 | 0.6509 | 0.3700 | 0.067 (2)* | |
O1B | 0.1502 (2) | 0.27672 (18) | 0.39171 (12) | 0.0549 (5) | |
O2B | 0.1623 (3) | 0.1091 (2) | 0.43483 (14) | 0.0693 (6) | |
O3B | 0.2520 (2) | 0.53685 (17) | 0.19402 (12) | 0.0595 (5) | |
O4B | 0.0244 (3) | 0.4002 (2) | 0.07246 (14) | 0.0745 (7) | |
N1B | −0.0319 (4) | 0.1358 (3) | 0.4752 (2) | 0.0659 (8) | |
H201 | −0.071 (3) | 0.179 (3) | 0.4685 (19) | 0.055 (9)* | |
H202 | −0.085 (4) | 0.063 (3) | 0.501 (2) | 0.076 (10)* | |
N2B | 0.2187 (4) | 0.6347 (3) | 0.0825 (2) | 0.0737 (9) | |
H203 | 0.163 (4) | 0.632 (3) | 0.033 (2) | 0.069 (10)* | |
H204 | 0.314 (5) | 0.710 (4) | 0.115 (3) | 0.115 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0373 (14) | 0.0431 (14) | 0.0555 (16) | 0.0202 (12) | 0.0084 (12) | 0.0219 (12) |
C2A | 0.085 (2) | 0.096 (2) | 0.111 (3) | 0.071 (2) | 0.050 (2) | 0.064 (2) |
C3A | 0.116 (3) | 0.148 (4) | 0.179 (4) | 0.112 (3) | 0.086 (3) | 0.099 (4) |
C4A | 0.139 (4) | 0.205 (5) | 0.175 (5) | 0.141 (4) | 0.115 (4) | 0.127 (4) |
C5A | 0.202 (5) | 0.291 (7) | 0.193 (5) | 0.207 (6) | 0.160 (5) | 0.194 (6) |
C6A | 0.130 (3) | 0.190 (4) | 0.142 (4) | 0.134 (4) | 0.096 (3) | 0.127 (4) |
C7A | 0.0403 (14) | 0.0395 (14) | 0.0419 (14) | 0.0235 (12) | 0.0018 (11) | 0.0110 (11) |
C8A | 0.0453 (15) | 0.0426 (14) | 0.0395 (14) | 0.0272 (12) | −0.0059 (12) | −0.0015 (11) |
C9A | 0.0574 (18) | 0.0459 (16) | 0.0524 (16) | 0.0235 (14) | −0.0053 (13) | 0.0126 (13) |
C10A | 0.0407 (15) | 0.0419 (15) | 0.0403 (14) | 0.0247 (13) | 0.0047 (12) | 0.0094 (12) |
C11A | 0.0557 (17) | 0.0408 (16) | 0.0455 (15) | 0.0278 (14) | −0.0027 (14) | 0.0035 (13) |
C12A | 0.0482 (16) | 0.0504 (16) | 0.0527 (16) | 0.0266 (14) | 0.0116 (13) | 0.0193 (13) |
O1A | 0.0493 (10) | 0.0434 (9) | 0.0432 (10) | 0.0295 (9) | −0.0064 (8) | 0.0031 (8) |
O2A | 0.0697 (13) | 0.0538 (12) | 0.0540 (11) | 0.0433 (10) | −0.0124 (9) | −0.0004 (9) |
O3A | 0.0659 (13) | 0.0413 (11) | 0.0710 (13) | 0.0182 (10) | −0.0279 (11) | 0.0113 (9) |
O4A | 0.0513 (11) | 0.0529 (11) | 0.0636 (12) | 0.0290 (10) | −0.0069 (9) | 0.0146 (9) |
N1A | 0.0722 (18) | 0.0456 (15) | 0.0522 (15) | 0.0357 (14) | −0.0170 (13) | −0.0007 (13) |
N2A | 0.075 (2) | 0.0448 (16) | 0.083 (2) | 0.0188 (16) | −0.0245 (17) | 0.0207 (14) |
C1B | 0.0521 (17) | 0.0443 (15) | 0.0549 (17) | 0.0258 (14) | 0.0089 (13) | 0.0256 (13) |
C2B | 0.053 (2) | 0.061 (2) | 0.098 (2) | 0.0271 (17) | 0.0022 (18) | 0.0321 (18) |
C3B | 0.051 (2) | 0.096 (3) | 0.170 (5) | 0.037 (2) | 0.021 (3) | 0.074 (3) |
C4B | 0.097 (4) | 0.136 (5) | 0.183 (5) | 0.079 (4) | 0.085 (4) | 0.112 (4) |
C5B | 0.123 (4) | 0.116 (4) | 0.117 (3) | 0.075 (3) | 0.074 (3) | 0.053 (3) |
C6B | 0.080 (2) | 0.071 (2) | 0.077 (2) | 0.0365 (19) | 0.0397 (19) | 0.0275 (19) |
C7B | 0.0551 (16) | 0.0393 (14) | 0.0370 (13) | 0.0275 (13) | 0.0023 (12) | 0.0122 (11) |
C8B | 0.0574 (17) | 0.0514 (16) | 0.0479 (15) | 0.0360 (14) | 0.0168 (13) | 0.0229 (12) |
C9B | 0.0591 (17) | 0.0460 (15) | 0.0537 (16) | 0.0294 (14) | 0.0062 (13) | 0.0223 (13) |
C10B | 0.0615 (18) | 0.0475 (15) | 0.0471 (15) | 0.0362 (14) | 0.0209 (14) | 0.0225 (12) |
C11B | 0.074 (2) | 0.0514 (17) | 0.0413 (15) | 0.0448 (17) | 0.0031 (14) | 0.0105 (13) |
C12B | 0.096 (2) | 0.0550 (18) | 0.0526 (17) | 0.0467 (18) | 0.0082 (16) | 0.0113 (14) |
O1B | 0.0694 (12) | 0.0586 (11) | 0.0623 (11) | 0.0470 (10) | 0.0303 (10) | 0.0343 (9) |
O2B | 0.0938 (15) | 0.0769 (14) | 0.0891 (15) | 0.0689 (13) | 0.0539 (13) | 0.0544 (12) |
O3B | 0.0688 (12) | 0.0460 (10) | 0.0514 (11) | 0.0306 (10) | −0.0066 (9) | 0.0171 (8) |
O4B | 0.0874 (16) | 0.0480 (12) | 0.0681 (13) | 0.0377 (12) | −0.0227 (12) | 0.0060 (10) |
N1B | 0.0785 (19) | 0.0733 (19) | 0.0854 (19) | 0.0583 (17) | 0.0451 (16) | 0.0484 (16) |
N2B | 0.097 (2) | 0.0552 (17) | 0.0562 (17) | 0.0436 (18) | −0.0120 (16) | 0.0172 (14) |
Geometric parameters (Å, º) top
C1A—C6A | 1.359 (4) | C1B—C2B | 1.381 (4) |
C1A—C2A | 1.362 (4) | C1B—C6B | 1.390 (4) |
C1A—C7A | 1.526 (4) | C1B—C7B | 1.533 (4) |
C2A—C3A | 1.388 (5) | C2B—C3B | 1.388 (5) |
C2A—H2A | 0.9300 | C2B—H2B | 0.9300 |
C3A—C4A | 1.317 (5) | C3B—C4B | 1.343 (6) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.343 (6) | C4B—C5B | 1.364 (6) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.381 (5) | C5B—C6B | 1.391 (5) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.521 (3) | C7B—C9B | 1.520 (3) |
C7A—C12A | 1.522 (3) | C7B—C12B | 1.523 (4) |
C7A—C9A | 1.536 (3) | C7B—C8B | 1.530 (3) |
C8A—O1A | 1.444 (3) | C8B—O1B | 1.445 (3) |
C8A—H8A1 | 0.9700 | C8B—H8B1 | 0.9700 |
C8A—H8A2 | 0.9700 | C8B—H8B2 | 0.9700 |
C9A—O3A | 1.442 (3) | C9B—O3B | 1.440 (3) |
C9A—H9A1 | 0.9700 | C9B—H9B1 | 0.9700 |
C9A—H9A2 | 0.9700 | C9B—H9B2 | 0.9700 |
C10A—O2A | 1.220 (3) | C10B—O2B | 1.214 (3) |
C10A—N1A | 1.324 (3) | C10B—O1B | 1.341 (3) |
C10A—O1A | 1.339 (3) | C10B—N1B | 1.329 (4) |
C11A—O4A | 1.213 (3) | C11B—O4B | 1.214 (3) |
C11A—N2A | 1.311 (3) | C11B—O3B | 1.327 (3) |
C11A—O3A | 1.339 (3) | C11B—N2B | 1.330 (4) |
C12A—H12A | 0.9600 | C12B—H12D | 0.9600 |
C12A—H12B | 0.9600 | C12B—H12E | 0.9600 |
C12A—H12C | 0.9600 | C12B—H12F | 0.9600 |
N1A—H101 | 0.86 (3) | N1B—H201 | 0.83 (3) |
N1A—H102 | 0.82 (3) | N1B—H202 | 0.87 (3) |
N2A—H103 | 0.90 (4) | N2B—H203 | 0.83 (3) |
N2A—H104 | 0.86 (4) | N2B—H204 | 0.86 (4) |
| | | |
C6A—C1A—C2A | 115.5 (3) | C2B—C1B—C6B | 117.0 (3) |
C6A—C1A—C7A | 122.9 (3) | C2B—C1B—C7B | 122.5 (3) |
C2A—C1A—C7A | 121.6 (2) | C6B—C1B—C7B | 120.5 (2) |
C1A—C2A—C3A | 122.3 (3) | C1B—C2B—C3B | 120.7 (4) |
C1A—C2A—H2A | 118.8 | C1B—C2B—H2B | 119.6 |
C3A—C2A—H2A | 118.8 | C3B—C2B—H2B | 119.6 |
C4A—C3A—C2A | 120.7 (4) | C4B—C3B—C2B | 121.6 (4) |
C4A—C3A—H3A | 119.6 | C4B—C3B—H3B | 119.2 |
C2A—C3A—H3A | 119.6 | C2B—C3B—H3B | 119.2 |
C3A—C4A—C5A | 118.6 (4) | C5B—C4B—C3B | 119.2 (4) |
C3A—C4A—H4A | 120.7 | C5B—C4B—H4B | 120.4 |
C5A—C4A—H4A | 120.7 | C3B—C4B—H4B | 120.4 |
C4A—C5A—C6A | 121.2 (4) | C4B—C5B—C6B | 120.3 (4) |
C4A—C5A—H5A | 119.4 | C4B—C5B—H5B | 119.9 |
C6A—C5A—H5A | 119.4 | C6B—C5B—H5B | 119.9 |
C1A—C6A—C5A | 121.6 (3) | C1B—C6B—C5B | 121.2 (3) |
C1A—C6A—H6A | 119.2 | C1B—C6B—H6B | 119.4 |
C5A—C6A—H6A | 119.2 | C5B—C6B—H6B | 119.4 |
C8A—C7A—C12A | 109.6 (2) | C9B—C7B—C12B | 109.2 (2) |
C8A—C7A—C1A | 112.7 (2) | C9B—C7B—C1B | 110.2 (2) |
C12A—C7A—C1A | 112.3 (2) | C12B—C7B—C1B | 113.1 (2) |
C8A—C7A—C9A | 105.8 (2) | C9B—C7B—C8B | 107.8 (2) |
C12A—C7A—C9A | 106.4 (2) | C12B—C7B—C8B | 110.1 (2) |
C1A—C7A—C9A | 109.6 (2) | C1B—C7B—C8B | 106.3 (2) |
O1A—C8A—C7A | 109.30 (18) | O1B—C8B—C7B | 108.6 (2) |
O1A—C8A—H8A1 | 109.8 | O1B—C8B—H8B1 | 110.0 |
C7A—C8A—H8A1 | 109.8 | C7B—C8B—H8B1 | 110.0 |
O1A—C8A—H8A2 | 109.8 | O1B—C8B—H8B2 | 110.0 |
C7A—C8A—H8A2 | 109.8 | C7B—C8B—H8B2 | 110.0 |
H8A1—C8A—H8A2 | 108.3 | H8B1—C8B—H8B2 | 108.3 |
O3A—C9A—C7A | 109.1 (2) | O3B—C9B—C7B | 108.2 (2) |
O3A—C9A—H9A1 | 109.9 | O3B—C9B—H9B1 | 110.1 |
C7A—C9A—H9A1 | 109.9 | C7B—C9B—H9B1 | 110.1 |
O3A—C9A—H9A2 | 109.9 | O3B—C9B—H9B2 | 110.1 |
C7A—C9A—H9A2 | 109.9 | C7B—C9B—H9B2 | 110.1 |
H9A1—C9A—H9A2 | 108.3 | H9B1—C9B—H9B2 | 108.4 |
O2A—C10A—N1A | 124.1 (2) | O2B—C10B—O1B | 122.9 (2) |
O2A—C10A—O1A | 123.2 (2) | O2B—C10B—N1B | 125.7 (2) |
N1A—C10A—O1A | 112.7 (2) | O1B—C10B—N1B | 111.5 (2) |
O4A—C11A—N2A | 126.2 (3) | O4B—C11B—O3B | 123.1 (2) |
O4A—C11A—O3A | 122.7 (2) | O4B—C11B—N2B | 124.7 (3) |
N2A—C11A—O3A | 111.1 (3) | O3B—C11B—N2B | 112.2 (3) |
C7A—C12A—H12A | 109.5 | C7B—C12B—H12D | 109.5 |
C7A—C12A—H12B | 109.5 | C7B—C12B—H12E | 109.5 |
H12A—C12A—H12B | 109.5 | H12D—C12B—H12E | 109.5 |
C7A—C12A—H12C | 109.5 | C7B—C12B—H12F | 109.5 |
H12A—C12A—H12C | 109.5 | H12D—C12B—H12F | 109.5 |
H12B—C12A—H12C | 109.5 | H12E—C12B—H12F | 109.5 |
C10A—O1A—C8A | 114.40 (18) | C10B—O1B—C8B | 116.13 (19) |
C11A—O3A—C9A | 117.9 (2) | C11B—O3B—C9B | 116.9 (2) |
C10A—N1A—H101 | 115.2 (18) | C10B—N1B—H201 | 118.6 (19) |
C10A—N1A—H102 | 118.5 (19) | C10B—N1B—H202 | 121 (2) |
H101—N1A—H102 | 124 (3) | H201—N1B—H202 | 119 (3) |
C11A—N2A—H103 | 121 (2) | C11B—N2B—H203 | 118 (2) |
C11A—N2A—H104 | 119 (2) | C11B—N2B—H204 | 118 (3) |
H103—N2A—H104 | 120 (3) | H203—N2B—H204 | 124 (3) |
| | | |
C6A—C1A—C2A—C3A | 0.2 (6) | C6B—C1B—C2B—C3B | 1.5 (4) |
C7A—C1A—C2A—C3A | −178.8 (3) | C7B—C1B—C2B—C3B | −179.8 (3) |
C1A—C2A—C3A—C4A | 0.3 (7) | C1B—C2B—C3B—C4B | −1.3 (6) |
C2A—C3A—C4A—C5A | 0.6 (9) | C2B—C3B—C4B—C5B | 0.2 (7) |
C3A—C4A—C5A—C6A | −1.8 (10) | C3B—C4B—C5B—C6B | 0.6 (7) |
C2A—C1A—C6A—C5A | −1.4 (7) | C2B—C1B—C6B—C5B | −0.8 (5) |
C7A—C1A—C6A—C5A | 177.5 (4) | C7B—C1B—C6B—C5B | −179.5 (3) |
C4A—C5A—C6A—C1A | 2.4 (9) | C4B—C5B—C6B—C1B | −0.3 (6) |
C6A—C1A—C7A—C8A | 18.4 (4) | C2B—C1B—C7B—C9B | 126.8 (3) |
C2A—C1A—C7A—C8A | −162.7 (3) | C6B—C1B—C7B—C9B | −54.6 (3) |
C6A—C1A—C7A—C12A | 142.8 (3) | C2B—C1B—C7B—C12B | 4.3 (3) |
C2A—C1A—C7A—C12A | −38.4 (3) | C6B—C1B—C7B—C12B | −177.1 (3) |
C6A—C1A—C7A—C9A | −99.1 (4) | C2B—C1B—C7B—C8B | −116.7 (3) |
C2A—C1A—C7A—C9A | 79.7 (3) | C6B—C1B—C7B—C8B | 62.0 (3) |
C12A—C7A—C8A—O1A | −62.1 (3) | C9B—C7B—C8B—O1B | −65.3 (3) |
C1A—C7A—C8A—O1A | 63.8 (3) | C12B—C7B—C8B—O1B | 53.7 (3) |
C9A—C7A—C8A—O1A | −176.43 (19) | C1B—C7B—C8B—O1B | 176.57 (19) |
C8A—C7A—C9A—O3A | −57.7 (3) | C12B—C7B—C9B—O3B | 65.4 (3) |
C12A—C7A—C9A—O3A | −174.2 (2) | C1B—C7B—C9B—O3B | −59.5 (3) |
C1A—C7A—C9A—O3A | 64.1 (3) | C8B—C7B—C9B—O3B | −175.1 (2) |
O2A—C10A—O1A—C8A | 1.0 (3) | O2B—C10B—O1B—C8B | 2.4 (4) |
N1A—C10A—O1A—C8A | −178.2 (2) | N1B—C10B—O1B—C8B | −179.3 (2) |
C7A—C8A—O1A—C10A | −169.4 (2) | C7B—C8B—O1B—C10B | −174.4 (2) |
O4A—C11A—O3A—C9A | 0.3 (4) | O4B—C11B—O3B—C9B | 0.7 (4) |
N2A—C11A—O3A—C9A | −177.9 (3) | N2B—C11B—O3B—C9B | −179.4 (3) |
C7A—C9A—O3A—C11A | −140.0 (2) | C7B—C9B—O3B—C11B | 165.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H101···O2Ai | 0.86 (3) | 2.09 (3) | 2.946 (3) | 176 (3) |
N1B—H201···O4Aii | 0.83 (3) | 2.26 (3) | 3.079 (3) | 170 (3) |
N1A—H102···O4Biii | 0.82 (3) | 2.25 (3) | 3.012 (4) | 154 (3) |
N1B—H202···O2Biv | 0.87 (3) | 2.10 (3) | 2.954 (3) | 167 (3) |
N2A—H104···O4Av | 0.86 (4) | 2.09 (4) | 2.936 (4) | 169 (3) |
N2B—H203···O4Biii | 0.83 (3) | 2.10 (3) | 2.914 (4) | 166 (3) |
C6B—H6B···O2Avi | 0.93 | 2.52 | 3.414 (4) | 162 |
C8A—H8A1···O2Bvii | 0.97 | 2.50 | 3.431 (3) | 160 |
N2B—H204···Cg1 | 0.86 (4) | 2.80 (4) | 3.640 (4) | 166 (4) |
N2A—H103···Cg2vii | 0.90 (4) | 2.72 (5) | 3.619 (4) | 169 (4) |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1, y−1, z; (iii) −x, −y+1, −z; (iv) −x, −y, −z+1; (v) −x+2, −y+3, −z+1; (vi) x, y−1, z; (vii) x, y+1, z. |
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