Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040833/su6255sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040833/su6255Isup2.hkl |
CCDC reference: 296679
The title compound was prepared using the Sonogashira coupling of 2-iodobenzylalcohol and N,N-dimethylpent-4-ynamide (Thorand & Krause, 1998). Single crystals were obtained by evaporation of a solution of (I) in diethylether/hexane (1:1 v/v).
Equivalent reflections, including Friedel pairs, were merged. H atoms attached to C atoms were positioned geometrically and refined as riding atoms [Csp2—H = 0.95 Å, Csecondary—H = 0.99 Å, with Uiso(H) = 1.2Ueq(parent C atom), and Cmethyl—H = 0.98 Å, with Uiso(H) = 1.5Ueq(parent Cmethyl atom). The hydroxyl H atoms were located in difference Fourier maps and refined isotropically [O—H = 0.80 (3) - 0.84 (4) Å].
The title compound, (I), was prepared for an investigation of the addition of nucleophiles to C≡C triple bonds and C—H activation in the benzylic position by homogeneous gold catalysts (Hashmi, 2004).
Compound (I) crystallizes with four independent molecules (A, B, C and D) per asymmetric unit. The molecular structure of molecule A is illustrated in Fig. 1. The dimensions of all four molecules are very similar. The amide groups are planar; the O2—C12—N1—C14 torsion angles are 175.9 (2), -179.4 (2), 179.2 (2) and -179.7 (2)° for molecules A, B, C and D, respectively. The N atoms show no significant deviations from planarity; the sum of the three valence angles about the N atoms are 359.9 (2), 360.0 (2), 360.0 (2) and 359.9 (2)° for N1A, N1B, N1C and N1D, respectively. The angles between the plane of the phenyl group and the plane of the N,N-dimethylamide group are 77.2 (1), 82.2 (1), 80.2 (1) and 74.6 (1)° for molecules A, B, C and D, respectively. This confirms the similarity of the four molecules.
The C1—O1 bond is coplanar with the phenyl ring; the torsion angles O1—C1—C2—C3 are 2.6 (3), 3.9 (4), 1.9 (4) and 0.4 (3)° for molecules A, B, C and D, respectively. This conformation results in contact distances between atoms O1 and H3 of 2.40, 2.43, 2.41 and 2.38 Å, for molecules A, B, C and D, respectively.
In the crystal structure the molecules are connected by intermolecular hydrogen bonds between the hydroxyl groups and the keto groups to form chains. Details of the hydrogen bonding are given in Table 1, and the crystal packing is illustrated in Figs. 2 and 3. Molecules A and C are hydrogen bonded to their symmetry-related molecules to form chains extending in the a direction (Fig. 2). Molecules in these chains are related by an a-glide plane. Molecules B and D are hydrogen bonded to one another and form alternating zigzag chains running in the c direction (Fig. 3). The hydrogen-bonded chains are connected by intermolecular C—H···π and C—H···O contacts. The crystal packing shows a number of intermolecular C—H···O interactions with H···O distances between 2.36 and 2.59 Å and five weak intermolecular Cmethylene—H···πphenyl interactions.
Each of the hydrogen-bonded motifs shows pseudo-symmetry. Molecules A and C are related by the pseudo-relationship xC≈ 0.60 - xA, yC≈ 1.02 - yA and zC≈ 1/4 + zA. This is a pseudo-twofold screw axis about (0.30, 0.51, z) with a translation of c/4. Thus molecule C and molecule A at (-x, -y, 1/2 + z) are related by a pseudo-translation vector (0.60, 1.02, -0.25). The coordinates of molecules B and D also show a pseudo-relationship: xD ≈ xB - 0.11, yD≈ 2.02 - yB and zD≈ 1/4 + zB. This is a pseudo-glide plane perpendicular to the b axis through y = 1.01 with an unusual translation vector of (-0.11, 0, 1/4). Thus molecule D and molecule B, at (1/2 + x, -y, z), are related by a pseudo-translation vector (-0.61, 2.02, 1/4). This shows the pseudo-symmetry between the AC and BD structures to be very similar.
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1996); software used to prepare material for publication: SHELXL97.
C14H17NO2 | F(000) = 1984 |
Mr = 231.29 | Dx = 1.214 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 234 reflections |
a = 14.166 (2) Å | θ = 3–23° |
b = 12.9093 (14) Å | µ = 0.08 mm−1 |
c = 27.669 (5) Å | T = 161 K |
V = 5060.1 (14) Å3 | Block, colorless |
Z = 16 | 0.50 × 0.36 × 0.30 mm |
Siemens SMART 1K CCD diffractometer | 4295 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.088 |
Graphite monochromator | θmax = 28.2°, θmin = 1.6° |
ω scans | h = −18→18 |
57442 measured reflections | k = −16→16 |
6075 independent reflections | l = −35→36 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.04P)2] where P = (Fo2 + 2Fc2)/3 |
6075 reflections | (Δ/σ)max = 0.001 |
637 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C14H17NO2 | V = 5060.1 (14) Å3 |
Mr = 231.29 | Z = 16 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 14.166 (2) Å | µ = 0.08 mm−1 |
b = 12.9093 (14) Å | T = 161 K |
c = 27.669 (5) Å | 0.50 × 0.36 × 0.30 mm |
Siemens SMART 1K CCD diffractometer | 4295 reflections with I > 2σ(I) |
57442 measured reflections | Rint = 0.088 |
6075 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 1 restraint |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.20 e Å−3 |
6075 reflections | Δρmin = −0.23 e Å−3 |
637 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
O1A | 0.37820 (13) | 0.15278 (14) | 0.05478 (7) | 0.0393 (6) | |
O2A | 0.02339 (12) | 0.71572 (12) | 0.07999 (7) | 0.0351 (6) | |
N1A | 0.05693 (15) | 0.71735 (16) | 0.15970 (8) | 0.0330 (7) | |
C1A | 0.29706 (17) | 0.21607 (18) | 0.05739 (10) | 0.0307 (8) | |
C2A | 0.20831 (17) | 0.15298 (18) | 0.05081 (8) | 0.0263 (8) | |
C3A | 0.21107 (18) | 0.04612 (18) | 0.04523 (9) | 0.0307 (8) | |
C4A | 0.1288 (2) | −0.01082 (19) | 0.04179 (9) | 0.0365 (9) | |
C5A | 0.04163 (19) | 0.0367 (2) | 0.04430 (10) | 0.0374 (9) | |
C6A | 0.03805 (18) | 0.1436 (2) | 0.04912 (10) | 0.0356 (9) | |
C7A | 0.12069 (17) | 0.20241 (18) | 0.05233 (9) | 0.0275 (8) | |
C8A | 0.11260 (16) | 0.31328 (19) | 0.05742 (9) | 0.0296 (8) | |
C9A | 0.09901 (16) | 0.40440 (19) | 0.05960 (9) | 0.0294 (8) | |
C10A | 0.07846 (17) | 0.51640 (17) | 0.06217 (9) | 0.0304 (8) | |
C11A | 0.08119 (17) | 0.55762 (17) | 0.11362 (9) | 0.0278 (8) | |
C12A | 0.05215 (16) | 0.66984 (18) | 0.11667 (9) | 0.0261 (8) | |
C13A | 0.0288 (2) | 0.82532 (19) | 0.16402 (11) | 0.0433 (10) | |
C14A | 0.0840 (2) | 0.6666 (2) | 0.20433 (10) | 0.0474 (11) | |
O1B | 0.33554 (16) | 1.35895 (16) | 0.25728 (7) | 0.0474 (7) | |
O2B | 0.32004 (12) | 0.80472 (13) | 0.43736 (7) | 0.0372 (6) | |
N1B | 0.47923 (15) | 0.80170 (15) | 0.43823 (8) | 0.0349 (7) | |
C1B | 0.3216 (2) | 1.29967 (19) | 0.29929 (10) | 0.0431 (10) | |
C2B | 0.30095 (17) | 1.36687 (18) | 0.34241 (9) | 0.0283 (8) | |
C3B | 0.29128 (16) | 1.47342 (19) | 0.33893 (10) | 0.0316 (8) | |
C4B | 0.27603 (17) | 1.53338 (19) | 0.37995 (10) | 0.0360 (9) | |
C5B | 0.26976 (19) | 1.4874 (2) | 0.42503 (10) | 0.0392 (9) | |
C6B | 0.27842 (18) | 1.3810 (2) | 0.42871 (10) | 0.0367 (9) | |
C7B | 0.29351 (16) | 1.31998 (18) | 0.38820 (9) | 0.0294 (8) | |
C8B | 0.30037 (17) | 1.2092 (2) | 0.39342 (9) | 0.0330 (9) | |
C9B | 0.30021 (17) | 1.1172 (2) | 0.39918 (10) | 0.0339 (9) | |
C10B | 0.29893 (17) | 1.00510 (18) | 0.40840 (10) | 0.0331 (8) | |
C11B | 0.39817 (17) | 0.96243 (18) | 0.41666 (9) | 0.0306 (8) | |
C12B | 0.39639 (18) | 0.84983 (18) | 0.43142 (8) | 0.0285 (8) | |
C13B | 0.4807 (2) | 0.6940 (2) | 0.45301 (11) | 0.0464 (11) | |
C14B | 0.57119 (19) | 0.8511 (2) | 0.43224 (11) | 0.0499 (10) | |
O1C | 0.21968 (14) | 0.83643 (15) | 0.29652 (9) | 0.0487 (7) | |
O2C | 0.58719 (13) | 0.30725 (14) | 0.32566 (7) | 0.0393 (7) | |
N1C | 0.55543 (15) | 0.30091 (16) | 0.40535 (8) | 0.0364 (8) | |
C1C | 0.30625 (17) | 0.78497 (19) | 0.30315 (11) | 0.0357 (9) | |
C2C | 0.38792 (17) | 0.85808 (18) | 0.29753 (9) | 0.0276 (8) | |
C3C | 0.37586 (18) | 0.96322 (18) | 0.28847 (9) | 0.0334 (8) | |
C4C | 0.4518 (2) | 1.02960 (19) | 0.28558 (10) | 0.0393 (9) | |
C5C | 0.5431 (2) | 0.9926 (2) | 0.29240 (10) | 0.0426 (10) | |
C6C | 0.55624 (19) | 0.8891 (2) | 0.30116 (10) | 0.0384 (9) | |
C7C | 0.48036 (18) | 0.82014 (19) | 0.30347 (9) | 0.0313 (8) | |
C8C | 0.49737 (18) | 0.7105 (2) | 0.30943 (10) | 0.0350 (9) | |
C9C | 0.51310 (18) | 0.6196 (2) | 0.31054 (10) | 0.0345 (9) | |
C10C | 0.53397 (18) | 0.50833 (19) | 0.31125 (9) | 0.0350 (9) | |
C11C | 0.53484 (17) | 0.46454 (19) | 0.36236 (9) | 0.0329 (8) | |
C12C | 0.56070 (17) | 0.35084 (19) | 0.36336 (10) | 0.0303 (8) | |
C13C | 0.5794 (2) | 0.1913 (2) | 0.40767 (12) | 0.0472 (11) | |
C14C | 0.5260 (2) | 0.3484 (2) | 0.45078 (10) | 0.0495 (11) | |
O1D | 0.24076 (15) | 0.67616 (15) | 0.50370 (7) | 0.0426 (7) | |
O2D | 0.21377 (12) | 1.21168 (13) | 0.69024 (7) | 0.0379 (6) | |
N1D | 0.37233 (15) | 1.21832 (16) | 0.68588 (8) | 0.0331 (7) | |
C1D | 0.22969 (18) | 0.73079 (18) | 0.54750 (9) | 0.0310 (8) | |
C2D | 0.19697 (15) | 0.65924 (18) | 0.58684 (9) | 0.0268 (8) | |
C3D | 0.18178 (15) | 0.55449 (18) | 0.57882 (10) | 0.0296 (8) | |
C4D | 0.15836 (17) | 0.48839 (19) | 0.61657 (11) | 0.0365 (9) | |
C5D | 0.14824 (17) | 0.52612 (19) | 0.66284 (10) | 0.0369 (9) | |
C6D | 0.16055 (18) | 0.6301 (2) | 0.67133 (10) | 0.0353 (9) | |
C7D | 0.18432 (16) | 0.69807 (19) | 0.63390 (9) | 0.0283 (8) | |
C8D | 0.19404 (17) | 0.8072 (2) | 0.64375 (9) | 0.0324 (8) | |
C9D | 0.19605 (17) | 0.89814 (19) | 0.65196 (9) | 0.0313 (8) | |
C10D | 0.19449 (17) | 1.00940 (18) | 0.66234 (9) | 0.0298 (8) | |
C11D | 0.29295 (17) | 1.05206 (18) | 0.67397 (9) | 0.0304 (8) | |
C12D | 0.29051 (18) | 1.16646 (19) | 0.68383 (9) | 0.0290 (8) | |
C13D | 0.3713 (2) | 1.33007 (19) | 0.69314 (11) | 0.0444 (10) | |
C14D | 0.46490 (18) | 1.1706 (2) | 0.67854 (11) | 0.0438 (10) | |
H1A | 0.30030 | 0.27000 | 0.03200 | 0.0370* | |
H1B | 0.29520 | 0.25120 | 0.08920 | 0.0370* | |
H1C | 0.418 (2) | 0.192 (2) | 0.0642 (10) | 0.042 (9)* | |
H3A | 0.27030 | 0.01170 | 0.04380 | 0.0370* | |
H4A | 0.13220 | −0.08380 | 0.03760 | 0.0440* | |
H5A | −0.01480 | −0.00300 | 0.04280 | 0.0450* | |
H6A | −0.02150 | 0.17740 | 0.05030 | 0.0430* | |
H10A | 0.01520 | 0.52950 | 0.04830 | 0.0360* | |
H10B | 0.12520 | 0.55440 | 0.04240 | 0.0360* | |
H11A | 0.03850 | 0.51560 | 0.13410 | 0.0330* | |
H11B | 0.14600 | 0.55010 | 0.12650 | 0.0330* | |
H13A | 0.03530 | 0.85950 | 0.13260 | 0.0650* | |
H13B | 0.06930 | 0.86010 | 0.18770 | 0.0650* | |
H13C | −0.03710 | 0.82910 | 0.17470 | 0.0650* | |
H14A | 0.09800 | 0.59350 | 0.19790 | 0.0710* | |
H14B | 0.03210 | 0.67140 | 0.22760 | 0.0710* | |
H14C | 0.14010 | 0.70050 | 0.21770 | 0.0710* | |
H1D | 0.37890 | 1.25800 | 0.30570 | 0.0520* | |
H1E | 0.26830 | 1.25130 | 0.29410 | 0.0520* | |
H1F | 0.326 (2) | 1.317 (3) | 0.2346 (13) | 0.065 (11)* | |
H3B | 0.29510 | 1.50590 | 0.30820 | 0.0380* | |
H4B | 0.26990 | 1.60640 | 0.37700 | 0.0430* | |
H5B | 0.25960 | 1.52830 | 0.45310 | 0.0470* | |
H6B | 0.27400 | 1.34910 | 0.45960 | 0.0440* | |
H10C | 0.26990 | 0.96920 | 0.38050 | 0.0400* | |
H10D | 0.25960 | 0.99080 | 0.43720 | 0.0400* | |
H11C | 0.43540 | 0.96990 | 0.38660 | 0.0370* | |
H11D | 0.42970 | 1.00350 | 0.44220 | 0.0370* | |
H13D | 0.48150 | 0.69000 | 0.48840 | 0.0700* | |
H13E | 0.53720 | 0.66030 | 0.44000 | 0.0700* | |
H13F | 0.42430 | 0.65890 | 0.44060 | 0.0700* | |
H14D | 0.56240 | 0.92220 | 0.42060 | 0.0750* | |
H14E | 0.60870 | 0.81200 | 0.40870 | 0.0750* | |
H14F | 0.60420 | 0.85240 | 0.46340 | 0.0750* | |
H1G | 0.31190 | 0.72840 | 0.27920 | 0.0430* | |
H1H | 0.30790 | 0.75370 | 0.33580 | 0.0430* | |
H1I | 0.185 (2) | 0.791 (2) | 0.3054 (11) | 0.050 (10)* | |
H3C | 0.31390 | 0.98980 | 0.28420 | 0.0400* | |
H4C | 0.44180 | 1.10090 | 0.27890 | 0.0470* | |
H5C | 0.59550 | 1.03840 | 0.29100 | 0.0510* | |
H6C | 0.61850 | 0.86370 | 0.30580 | 0.0460* | |
H10E | 0.59630 | 0.49620 | 0.29610 | 0.0420* | |
H10F | 0.48590 | 0.47120 | 0.29190 | 0.0420* | |
H11E | 0.58080 | 0.50380 | 0.38210 | 0.0390* | |
H11F | 0.47160 | 0.47370 | 0.37700 | 0.0390* | |
H13G | 0.56280 | 0.15790 | 0.37700 | 0.0710* | |
H13H | 0.54430 | 0.15860 | 0.43410 | 0.0710* | |
H13I | 0.64730 | 0.18370 | 0.41350 | 0.0710* | |
H14G | 0.51490 | 0.42260 | 0.44570 | 0.0740* | |
H14H | 0.57570 | 0.33910 | 0.47500 | 0.0740* | |
H14I | 0.46770 | 0.31550 | 0.46210 | 0.0740* | |
H1J | 0.18300 | 0.78700 | 0.54310 | 0.0370* | |
H1K | 0.29060 | 0.76260 | 0.55690 | 0.0370* | |
H1L | 0.262 (2) | 0.718 (2) | 0.4851 (12) | 0.055 (10)* | |
H3D | 0.18750 | 0.52750 | 0.54700 | 0.0360* | |
H4D | 0.14930 | 0.41670 | 0.61040 | 0.0440* | |
H5D | 0.13290 | 0.48060 | 0.68870 | 0.0440* | |
H6D | 0.15280 | 0.65620 | 0.70320 | 0.0420* | |
H10G | 0.15210 | 1.02240 | 0.69010 | 0.0360* | |
H10H | 0.16860 | 1.04670 | 0.63400 | 0.0360* | |
H11G | 0.31850 | 1.01560 | 0.70260 | 0.0360* | |
H11H | 0.33570 | 1.03830 | 0.64640 | 0.0360* | |
H13J | 0.32120 | 1.36100 | 0.67350 | 0.0670* | |
H13K | 0.43240 | 1.35920 | 0.68350 | 0.0670* | |
H13L | 0.35980 | 1.34530 | 0.72730 | 0.0670* | |
H14J | 0.45970 | 1.09540 | 0.68260 | 0.0660* | |
H14K | 0.50970 | 1.19840 | 0.70220 | 0.0660* | |
H14L | 0.48740 | 1.18610 | 0.64580 | 0.0660* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0248 (10) | 0.0328 (10) | 0.0603 (13) | 0.0010 (9) | −0.0049 (9) | −0.0073 (9) |
O2A | 0.0356 (11) | 0.0303 (10) | 0.0395 (11) | 0.0084 (8) | −0.0028 (9) | 0.0015 (8) |
N1A | 0.0323 (13) | 0.0324 (12) | 0.0343 (13) | 0.0025 (9) | 0.0011 (10) | −0.0034 (10) |
C1A | 0.0285 (14) | 0.0283 (13) | 0.0352 (15) | 0.0026 (10) | −0.0010 (11) | 0.0001 (11) |
C2A | 0.0295 (14) | 0.0293 (13) | 0.0201 (13) | −0.0001 (10) | −0.0018 (10) | −0.0010 (10) |
C3A | 0.0343 (15) | 0.0270 (14) | 0.0309 (15) | 0.0026 (11) | −0.0073 (11) | −0.0017 (11) |
C4A | 0.0496 (17) | 0.0237 (13) | 0.0362 (16) | −0.0025 (13) | −0.0098 (13) | −0.0025 (11) |
C5A | 0.0353 (15) | 0.0362 (15) | 0.0406 (17) | −0.0097 (12) | −0.0054 (12) | 0.0013 (13) |
C6A | 0.0283 (14) | 0.0369 (15) | 0.0415 (17) | 0.0009 (12) | −0.0024 (12) | −0.0006 (12) |
C7A | 0.0289 (14) | 0.0276 (13) | 0.0261 (14) | 0.0003 (11) | 0.0004 (11) | 0.0017 (10) |
C8A | 0.0235 (13) | 0.0340 (14) | 0.0313 (14) | 0.0025 (11) | 0.0005 (11) | −0.0004 (11) |
C9A | 0.0229 (13) | 0.0320 (15) | 0.0332 (15) | 0.0015 (11) | −0.0013 (11) | −0.0019 (12) |
C10A | 0.0257 (13) | 0.0256 (13) | 0.0398 (15) | 0.0040 (10) | −0.0031 (12) | −0.0010 (11) |
C11A | 0.0226 (13) | 0.0259 (13) | 0.0348 (15) | −0.0018 (10) | 0.0028 (11) | 0.0026 (12) |
C12A | 0.0166 (12) | 0.0254 (13) | 0.0362 (15) | −0.0002 (10) | 0.0040 (11) | 0.0014 (12) |
C13A | 0.0447 (17) | 0.0342 (15) | 0.0510 (19) | 0.0006 (13) | 0.0062 (14) | −0.0097 (13) |
C14A | 0.0513 (19) | 0.0537 (19) | 0.0372 (17) | 0.0054 (15) | −0.0010 (14) | −0.0006 (14) |
O1B | 0.0691 (14) | 0.0430 (12) | 0.0300 (11) | −0.0177 (10) | 0.0000 (10) | −0.0009 (10) |
O2B | 0.0309 (10) | 0.0319 (10) | 0.0488 (12) | −0.0058 (8) | 0.0011 (9) | 0.0097 (8) |
N1B | 0.0309 (12) | 0.0377 (13) | 0.0360 (13) | 0.0025 (10) | 0.0011 (10) | 0.0083 (10) |
C1B | 0.062 (2) | 0.0324 (15) | 0.0350 (17) | −0.0046 (13) | −0.0006 (14) | 0.0027 (13) |
C2B | 0.0222 (13) | 0.0289 (14) | 0.0338 (14) | −0.0041 (10) | −0.0029 (10) | 0.0009 (11) |
C3B | 0.0212 (13) | 0.0332 (15) | 0.0403 (16) | −0.0008 (11) | −0.0023 (11) | 0.0059 (12) |
C4B | 0.0241 (13) | 0.0272 (14) | 0.0566 (19) | 0.0025 (11) | 0.0028 (12) | −0.0012 (13) |
C5B | 0.0322 (15) | 0.0384 (16) | 0.0469 (18) | 0.0016 (12) | 0.0064 (13) | −0.0101 (14) |
C6B | 0.0324 (15) | 0.0411 (16) | 0.0365 (17) | −0.0005 (12) | 0.0037 (12) | 0.0019 (13) |
C7B | 0.0220 (12) | 0.0270 (13) | 0.0392 (16) | −0.0009 (10) | 0.0005 (11) | 0.0019 (12) |
C8B | 0.0279 (14) | 0.0383 (16) | 0.0328 (15) | 0.0005 (11) | 0.0021 (11) | 0.0050 (12) |
C9B | 0.0297 (15) | 0.0356 (16) | 0.0365 (16) | 0.0007 (12) | 0.0034 (12) | 0.0051 (12) |
C10B | 0.0316 (14) | 0.0293 (14) | 0.0385 (16) | −0.0014 (11) | 0.0050 (12) | 0.0067 (12) |
C11B | 0.0306 (14) | 0.0301 (14) | 0.0311 (14) | −0.0045 (11) | 0.0023 (11) | 0.0027 (11) |
C12B | 0.0336 (15) | 0.0301 (14) | 0.0219 (13) | −0.0010 (11) | 0.0022 (11) | 0.0012 (10) |
C13B | 0.0493 (19) | 0.0409 (17) | 0.049 (2) | 0.0103 (14) | 0.0009 (14) | 0.0047 (14) |
C14B | 0.0283 (15) | 0.069 (2) | 0.0523 (19) | −0.0028 (14) | 0.0001 (14) | 0.0187 (16) |
O1C | 0.0267 (11) | 0.0394 (11) | 0.0799 (16) | 0.0008 (9) | 0.0055 (10) | 0.0169 (11) |
O2C | 0.0405 (11) | 0.0359 (11) | 0.0415 (12) | 0.0115 (9) | 0.0015 (9) | −0.0030 (9) |
N1C | 0.0296 (13) | 0.0379 (13) | 0.0418 (14) | 0.0055 (10) | 0.0006 (10) | 0.0038 (11) |
C1C | 0.0307 (15) | 0.0306 (14) | 0.0457 (17) | 0.0030 (11) | 0.0000 (12) | −0.0013 (12) |
C2C | 0.0310 (14) | 0.0293 (13) | 0.0226 (13) | 0.0009 (11) | 0.0024 (11) | −0.0003 (10) |
C3C | 0.0372 (15) | 0.0329 (14) | 0.0301 (15) | 0.0035 (12) | 0.0045 (12) | 0.0025 (12) |
C4C | 0.0499 (18) | 0.0270 (14) | 0.0410 (17) | −0.0021 (13) | 0.0118 (14) | 0.0015 (12) |
C5C | 0.0422 (17) | 0.0413 (16) | 0.0444 (18) | −0.0145 (13) | 0.0124 (13) | −0.0037 (14) |
C6C | 0.0303 (15) | 0.0466 (17) | 0.0384 (17) | −0.0043 (12) | 0.0031 (12) | −0.0035 (13) |
C7C | 0.0345 (15) | 0.0320 (14) | 0.0273 (14) | 0.0037 (11) | 0.0058 (11) | −0.0017 (11) |
C8C | 0.0289 (14) | 0.0403 (17) | 0.0358 (16) | 0.0027 (12) | 0.0036 (11) | 0.0018 (13) |
C9C | 0.0276 (14) | 0.0372 (16) | 0.0388 (16) | 0.0057 (12) | 0.0029 (12) | 0.0019 (12) |
C10C | 0.0304 (15) | 0.0323 (14) | 0.0422 (17) | 0.0105 (11) | 0.0018 (12) | −0.0017 (12) |
C11C | 0.0215 (13) | 0.0366 (15) | 0.0406 (16) | 0.0072 (11) | 0.0004 (11) | −0.0049 (12) |
C12C | 0.0193 (12) | 0.0341 (15) | 0.0375 (16) | 0.0021 (11) | −0.0030 (11) | 0.0011 (13) |
C13C | 0.0404 (17) | 0.0431 (18) | 0.058 (2) | 0.0004 (14) | −0.0017 (15) | 0.0098 (15) |
C14C | 0.0414 (18) | 0.069 (2) | 0.0380 (17) | 0.0151 (15) | 0.0027 (14) | 0.0023 (14) |
O1D | 0.0528 (13) | 0.0378 (11) | 0.0371 (13) | −0.0110 (10) | 0.0090 (9) | −0.0013 (10) |
O2D | 0.0318 (11) | 0.0325 (10) | 0.0494 (12) | 0.0021 (8) | 0.0011 (9) | −0.0124 (8) |
N1D | 0.0285 (12) | 0.0350 (12) | 0.0357 (13) | −0.0034 (10) | 0.0010 (10) | 0.0001 (10) |
C1D | 0.0248 (13) | 0.0279 (13) | 0.0402 (16) | 0.0011 (11) | 0.0005 (11) | −0.0004 (12) |
C2D | 0.0144 (11) | 0.0273 (13) | 0.0388 (15) | 0.0015 (10) | −0.0008 (10) | 0.0019 (11) |
C3D | 0.0193 (12) | 0.0285 (14) | 0.0411 (16) | −0.0015 (10) | 0.0016 (11) | −0.0061 (12) |
C4D | 0.0246 (13) | 0.0253 (13) | 0.0596 (19) | −0.0005 (11) | 0.0010 (13) | 0.0021 (14) |
C5D | 0.0283 (15) | 0.0349 (15) | 0.0476 (18) | 0.0012 (12) | 0.0017 (12) | 0.0108 (13) |
C6D | 0.0284 (14) | 0.0414 (16) | 0.0362 (16) | 0.0041 (12) | 0.0000 (12) | −0.0002 (13) |
C7D | 0.0203 (12) | 0.0255 (13) | 0.0390 (16) | 0.0017 (10) | −0.0023 (11) | −0.0028 (11) |
C8D | 0.0235 (13) | 0.0374 (16) | 0.0363 (15) | 0.0016 (11) | 0.0015 (11) | −0.0031 (12) |
C9D | 0.0290 (14) | 0.0318 (15) | 0.0331 (15) | −0.0008 (11) | 0.0026 (11) | −0.0037 (11) |
C10D | 0.0305 (14) | 0.0281 (13) | 0.0307 (15) | 0.0015 (11) | 0.0034 (11) | −0.0033 (11) |
C11D | 0.0278 (14) | 0.0310 (14) | 0.0324 (15) | 0.0021 (11) | −0.0009 (11) | −0.0023 (11) |
C12D | 0.0328 (15) | 0.0312 (14) | 0.0229 (13) | 0.0024 (12) | −0.0016 (11) | −0.0017 (11) |
C13D | 0.0477 (18) | 0.0358 (16) | 0.0498 (19) | −0.0106 (13) | −0.0051 (14) | 0.0001 (13) |
C14D | 0.0262 (15) | 0.063 (2) | 0.0422 (17) | −0.0012 (14) | −0.0011 (13) | −0.0050 (15) |
O1A—C1A | 1.412 (3) | C5B—H5B | 0.9500 |
O2A—C12A | 1.244 (3) | C6B—H6B | 0.9500 |
O1A—H1C | 0.80 (3) | C10B—H10C | 0.9900 |
O1B—C1B | 1.406 (3) | C10B—H10D | 0.9900 |
O2B—C12B | 1.239 (3) | C11B—H11D | 0.9900 |
O1B—H1F | 0.84 (4) | C11B—H11C | 0.9900 |
O1C—C1C | 1.407 (3) | C13B—H13D | 0.9800 |
O2C—C12C | 1.243 (3) | C13B—H13F | 0.9800 |
O1C—H1I | 0.80 (3) | C13B—H13E | 0.9800 |
O1D—C1D | 1.411 (3) | C14B—H14E | 0.9800 |
O2D—C12D | 1.247 (3) | C14B—H14D | 0.9800 |
O1D—H1L | 0.80 (3) | C14B—H14F | 0.9800 |
N1A—C14A | 1.450 (4) | C1C—C2C | 1.501 (3) |
N1A—C13A | 1.455 (3) | C2C—C7C | 1.408 (4) |
N1A—C12A | 1.341 (3) | C2C—C3C | 1.391 (3) |
N1B—C14B | 1.460 (3) | C3C—C4C | 1.378 (4) |
N1B—C13B | 1.449 (3) | C4C—C5C | 1.392 (4) |
N1B—C12B | 1.341 (3) | C5C—C6C | 1.371 (4) |
N1C—C14C | 1.459 (4) | C6C—C7C | 1.397 (4) |
N1C—C12C | 1.331 (3) | C7C—C8C | 1.445 (4) |
N1C—C13C | 1.457 (3) | C8C—C9C | 1.195 (4) |
N1D—C14D | 1.463 (3) | C9C—C10C | 1.467 (4) |
N1D—C12D | 1.340 (3) | C10C—C11C | 1.523 (4) |
N1D—C13D | 1.457 (3) | C11C—C12C | 1.513 (3) |
C1A—C2A | 1.509 (3) | C1C—H1G | 0.9900 |
C2A—C3A | 1.389 (3) | C1C—H1H | 0.9900 |
C2A—C7A | 1.396 (3) | C3C—H3C | 0.9500 |
C3A—C4A | 1.381 (4) | C4C—H4C | 0.9500 |
C4A—C5A | 1.381 (4) | C5C—H5C | 0.9500 |
C5A—C6A | 1.387 (4) | C6C—H6C | 0.9500 |
C6A—C7A | 1.398 (4) | C10C—H10F | 0.9900 |
C7A—C8A | 1.443 (3) | C10C—H10E | 0.9900 |
C8A—C9A | 1.194 (3) | C11C—H11E | 0.9900 |
C9A—C10A | 1.477 (3) | C11C—H11F | 0.9900 |
C10A—C11A | 1.520 (3) | C13C—H13G | 0.9800 |
C11A—C12A | 1.508 (3) | C13C—H13H | 0.9800 |
C1A—H1A | 0.9900 | C13C—H13I | 0.9800 |
C1A—H1B | 0.9900 | C14C—H14I | 0.9800 |
C3A—H3A | 0.9500 | C14C—H14H | 0.9800 |
C4A—H4A | 0.9500 | C14C—H14G | 0.9800 |
C5A—H5A | 0.9500 | C1D—C2D | 1.501 (3) |
C6A—H6A | 0.9500 | C2D—C3D | 1.387 (3) |
C10A—H10B | 0.9900 | C2D—C7D | 1.407 (4) |
C10A—H10A | 0.9900 | C3D—C4D | 1.389 (4) |
C11A—H11B | 0.9900 | C4D—C5D | 1.377 (4) |
C11A—H11A | 0.9900 | C5D—C6D | 1.374 (4) |
C13A—H13C | 0.9800 | C6D—C7D | 1.399 (4) |
C13A—H13B | 0.9800 | C7D—C8D | 1.442 (4) |
C13A—H13A | 0.9800 | C8D—C9D | 1.196 (4) |
C14A—H14A | 0.9800 | C9D—C10D | 1.465 (3) |
C14A—H14C | 0.9800 | C10D—C11D | 1.534 (3) |
C14A—H14B | 0.9800 | C11D—C12D | 1.502 (3) |
C1B—C2B | 1.504 (4) | C1D—H1J | 0.9900 |
C2B—C3B | 1.386 (3) | C1D—H1K | 0.9900 |
C2B—C7B | 1.408 (3) | C3D—H3D | 0.9500 |
C3B—C4B | 1.391 (4) | C4D—H4D | 0.9500 |
C4B—C5B | 1.384 (4) | C5D—H5D | 0.9500 |
C5B—C6B | 1.383 (4) | C6D—H6D | 0.9500 |
C6B—C7B | 1.387 (4) | C10D—H10G | 0.9900 |
C7B—C8B | 1.441 (3) | C10D—H10H | 0.9900 |
C8B—C9B | 1.198 (4) | C11D—H11G | 0.9900 |
C9B—C10B | 1.470 (3) | C11D—H11H | 0.9900 |
C10B—C11B | 1.527 (3) | C13D—H13J | 0.9800 |
C11B—C12B | 1.510 (3) | C13D—H13K | 0.9800 |
C1B—H1D | 0.9900 | C13D—H13L | 0.9800 |
C1B—H1E | 0.9900 | C14D—H14J | 0.9800 |
C3B—H3B | 0.9500 | C14D—H14K | 0.9800 |
C4B—H4B | 0.9500 | C14D—H14L | 0.9800 |
O1A···O2Ai | 2.757 (3) | C12C···H4Bxiv | 3.0400 |
O1A···C5Aii | 3.380 (3) | C12C···H1Ii | 3.00 (3) |
O1B···C5Diii | 3.397 (3) | C12D···H1Bxii | 3.0900 |
O1B···O2Div | 2.747 (3) | C14A···H11A | 2.8300 |
O1C···C5Cv | 3.338 (3) | C14A···H11B | 2.7700 |
O1C···O2Cvi | 2.759 (3) | C14B···H11C | 2.7700 |
O1D···C14Cvi | 3.391 (4) | C14B···H11D | 2.8200 |
O1D···O2B | 2.718 (3) | C14C···H11E | 2.8700 |
O1D···C5Bvii | 3.293 (3) | C14C···H11F | 2.7200 |
O2A···O1Avi | 2.757 (3) | C14D···H11G | 2.9600 |
O2A···C1Avi | 3.383 (3) | C14D···H11H | 2.6600 |
O2B···O1D | 2.718 (3) | H1A···C8A | 2.8100 |
O2C···C14Ai | 3.374 (3) | H1A···H6Bviii | 2.4800 |
O2C···C1Ci | 3.382 (3) | H1B···C8A | 2.8500 |
O2C···O1Ci | 2.759 (3) | H1B···C12Dviii | 3.0900 |
O1A···H3A | 2.4000 | H1B···H4Div | 2.3500 |
O1A···H10Hviii | 2.6700 | H1B···O2Dviii | 2.8400 |
O1A···H14Fix | 2.5400 | H1C···C12Ai | 2.98 (3) |
O1A···H5Aii | 2.4800 | H1C···O2Ai | 1.96 (3) |
O1B···H5Diii | 2.5000 | H1D···C8B | 2.7400 |
O1B···H3B | 2.4300 | H1D···H4C | 2.3400 |
O1B···H13Liv | 2.8900 | H1E···C8B | 2.8400 |
O1B···H10Fx | 2.7500 | H1F···H5Diii | 2.5300 |
O1C···H5Cv | 2.3900 | H1F···O2Div | 1.92 (4) |
O1C···H3C | 2.4100 | H1F···C13Div | 3.03 (3) |
O1D···H14Hvi | 2.4800 | H1F···C12Div | 2.91 (4) |
O1D···H10Bxi | 2.6900 | H1G···C8C | 2.7700 |
O1D···H5Bvii | 2.3800 | H1G···H6Div | 2.3500 |
O1D···H3D | 2.3800 | H1H···H4Bvii | 2.2800 |
O2A···H13Div | 2.5600 | H1H···C8C | 2.8400 |
O2A···H1Cvi | 1.96 (3) | H1H···O2B | 2.8900 |
O2A···H10B | 2.7400 | H1I···O2Cvi | 1.96 (3) |
O2A···H13A | 2.3600 | H1I···C12Cvi | 3.00 (3) |
O2A···H1Kiv | 2.7800 | H1I···H5Cv | 2.5700 |
O2A···H10A | 2.5600 | H1J···C8D | 2.8000 |
O2B···H13F | 2.3900 | H1K···O2Axi | 2.7800 |
O2B···H10C | 2.7400 | H1K···C8D | 2.8200 |
O2B···H10D | 2.5500 | H1K···C12Axi | 3.0200 |
O2B···H1H | 2.8900 | H1K···H4Axii | 2.3300 |
O2B···H1L | 1.92 (3) | H1L···C12B | 2.95 (3) |
O2B···H13Ivi | 2.5400 | H1L···O2B | 1.92 (3) |
O2C···H14Bi | 2.8400 | H3A···O1A | 2.4000 |
O2C···H10E | 2.5800 | H3B···O1B | 2.4300 |
O2C···H1Ii | 1.96 (3) | H3C···O1C | 2.4100 |
O2C···H13G | 2.4200 | H3D···O1D | 2.3800 |
O2C···H10F | 2.7200 | H4A···C12Bviii | 3.0900 |
O2D···H10H | 2.7100 | H4A···H1Kviii | 2.3300 |
O2D···H13J | 2.5000 | H4B···C12Cv | 3.0400 |
O2D···H13L | 2.8800 | H4B···H1Hx | 2.2800 |
O2D···H10G | 2.5900 | H4C···H1D | 2.3400 |
O2D···H1Bxii | 2.8400 | H4D···H1Bxi | 2.3500 |
C1A···O2Ai | 3.383 (3) | H4D···C1Axi | 3.0700 |
C1B···O2Div | 3.263 (3) | H5A···O1Axiii | 2.4800 |
C1C···O2Cvi | 3.382 (3) | H5B···O1Dx | 2.3800 |
C2B···C11Cx | 3.588 (3) | H5C···H1Ixiv | 2.5700 |
C2C···C11B | 3.564 (4) | H5C···O1Cxiv | 2.3900 |
C2D···C11Axi | 3.485 (3) | H6A···H1Jxvi | 2.3400 |
C3A···C11Dviii | 3.563 (4) | H6B···H1Axii | 2.4800 |
C3A···C10Dviii | 3.538 (4) | H10A···O2A | 2.5600 |
C3B···C11Cx | 3.513 (3) | H10B···C3Div | 2.9100 |
C3B···C10Cx | 3.551 (3) | H10B···O2A | 2.7400 |
C3C···C11B | 3.561 (4) | H10B···O1Div | 2.6900 |
C3C···C10B | 3.534 (4) | H10B···C1Div | 3.0700 |
C3D···C11Axi | 3.493 (3) | H10C···O2B | 2.7400 |
C3D···C10Axi | 3.463 (3) | H10C···C3C | 2.9600 |
C4A···C11Bviii | 3.500 (4) | H10D···O2B | 2.5500 |
C4A···C12Bviii | 3.562 (3) | H10E···O2C | 2.5800 |
C4B···C12Cv | 3.428 (3) | H10E···C3Bxiv | 3.0300 |
C4B···C11Cv | 3.451 (3) | H10F···C3Bvii | 3.0500 |
C5A···O1Axiii | 3.380 (3) | H10F···O2C | 2.7200 |
C5B···O1Dx | 3.293 (3) | H10F···O1Bvii | 2.7500 |
C5C···O1Cxiv | 3.338 (3) | H10G···O2D | 2.5900 |
C6A···C14Dviii | 3.598 (4) | H10H···O1Axii | 2.6700 |
C6B···C14Cx | 3.585 (4) | H10H···C1Axii | 3.0800 |
C6C···C14Dxv | 3.492 (4) | H10H···O2D | 2.7100 |
C7C···C14Dxv | 3.545 (4) | H10H···C3Axii | 2.9900 |
C8A···C14Civ | 3.573 (4) | H11A···C5Dxvi | 2.8100 |
C8B···C14Bv | 3.507 (4) | H11A···C14A | 2.8300 |
C9A···C14Civ | 3.567 (4) | H11A···H13Kviii | 2.4700 |
C9B···C14Bv | 3.396 (4) | H11A···H14A | 2.2000 |
C10A···C3Div | 3.463 (3) | H11A···C4Dxvi | 2.8300 |
C10B···C3C | 3.534 (4) | H11B···C7Div | 3.0800 |
C10C···C3Bvii | 3.551 (3) | H11B···C2Div | 2.8500 |
C10D···C3Axii | 3.538 (4) | H11B···C5Div | 3.1000 |
C11A···C3Div | 3.493 (3) | H11B···C14A | 2.7700 |
C11A···C2Div | 3.485 (3) | H11B···H14A | 2.1600 |
C11A···C4Dxvi | 3.446 (3) | H11B···C3Div | 2.7700 |
C11B···C2C | 3.564 (4) | H11B···C4Div | 2.9000 |
C11B···C3C | 3.561 (4) | H11C···C14B | 2.7700 |
C11B···C4Axii | 3.500 (4) | H11C···H14D | 2.1200 |
C11C···C4Bxiv | 3.451 (3) | H11C···C2C | 2.9300 |
C11C···C3Bvii | 3.513 (3) | H11C···C7C | 3.0700 |
C11C···C2Bvii | 3.588 (3) | H11C···C4C | 2.9100 |
C11D···C3Axii | 3.563 (4) | H11C···C5C | 3.0300 |
C12B···C4Axii | 3.562 (3) | H11C···C3C | 2.8400 |
C12C···C4Bxiv | 3.428 (3) | H11C···C6C | 3.1000 |
C14A···O2Cvi | 3.374 (3) | H11D···H13Hx | 2.5900 |
C14B···C9Bxiv | 3.396 (4) | H11D···C14B | 2.8200 |
C14B···C8Bxiv | 3.507 (4) | H11D···C5Axii | 2.8900 |
C14C···C9Axi | 3.567 (4) | H11D···H14D | 2.2300 |
C14C···C6Bvii | 3.585 (4) | H11D···C4Axii | 2.8800 |
C14C···C8Axi | 3.573 (4) | H11E···C4Bxiv | 2.8100 |
C14D···C6Axii | 3.598 (4) | H11E···C14C | 2.8700 |
C1A···H10Hviii | 3.0800 | H11E···H14G | 2.2500 |
C1A···H14Fix | 3.0800 | H11E···C5Bxiv | 2.9300 |
C1A···H4Div | 3.0700 | H11F···H14G | 2.1000 |
C1D···H10Bxi | 3.0700 | H11F···C14C | 2.7200 |
C1D···H14Hvi | 3.1000 | H11F···C2Bvii | 2.9400 |
C2A···H11Hviii | 3.0900 | H11F···C3Bvii | 2.7600 |
C2B···H11Fx | 2.9400 | H11F···C4Bvii | 2.8800 |
C2C···H14Kxv | 3.1000 | H11G···H14J | 2.3200 |
C2C···H11C | 2.9300 | H11G···H13Bxi | 2.5900 |
C2D···H11Bxi | 2.8500 | H11G···C14D | 2.9600 |
C3A···H10Hviii | 2.9900 | H11H···H14J | 2.1500 |
C3A···H11Hviii | 2.8800 | H11H···C14D | 2.6600 |
C3B···H10Ev | 3.0300 | H11H···C3Axii | 2.8800 |
C3B···H10Fx | 3.0500 | H11H···C4Axii | 3.0100 |
C3B···H11Fx | 2.7600 | H11H···C2Axii | 3.0900 |
C3C···H10C | 2.9600 | H13A···O2A | 2.3600 |
C3C···H10Giv | 2.8500 | H13B···H11Giv | 2.5900 |
C3C···H11C | 2.8400 | H13B···H14C | 2.4400 |
C3D···H10Bxi | 2.9100 | H13C···O2Dxvii | 2.5900 |
C3D···H11Bxi | 2.7700 | H13C···H10Gxvii | 2.5500 |
C4A···H11Dviii | 2.8800 | H13C···C10Dxvii | 3.0700 |
C4A···H11Hviii | 3.0100 | H13D···O2Axi | 2.5600 |
C4B···H11Fx | 2.8800 | H13E···H14E | 2.3700 |
C4B···H11Ev | 2.8100 | H13F···O2B | 2.3900 |
C4C···H10Giv | 3.0300 | H13G···O2C | 2.4200 |
C4C···H11C | 2.9100 | H13H···H11Dvii | 2.5900 |
C4D···H11Bxi | 2.9000 | H13H···H14I | 2.4200 |
C5A···H11Dviii | 2.8900 | H13J···O2D | 2.5000 |
C5B···H11Ev | 2.9300 | H13K···H11Axii | 2.4700 |
C5C···H11C | 3.0300 | H13K···H14L | 2.5900 |
C5D···H11Bxi | 3.1000 | H13K···H14K | 2.4000 |
C6A···H14Lviii | 2.7500 | H13L···O2D | 2.8800 |
C6B···H14Ix | 2.9600 | H14A···H11B | 2.1600 |
C6C···H11C | 3.1000 | H14A···H11A | 2.2000 |
C7A···H14Lviii | 3.0100 | H14A···C11A | 2.3900 |
C7C···H14Kxv | 2.8200 | H14B···O2Cvi | 2.8400 |
C7C···H11C | 3.0700 | H14C···H13B | 2.4400 |
C7D···H11Bxi | 3.0800 | H14D···C11B | 2.3900 |
C8A···H14Iiv | 2.8700 | H14D···H11D | 2.2300 |
C8A···H1A | 2.8100 | H14D···H11C | 2.1200 |
C8A···H1B | 2.8500 | H14E···H13E | 2.3700 |
C8B···H1D | 2.7400 | H14E···C9Bxiv | 2.8700 |
C8B···H14Ev | 2.7600 | H14E···C8Bxiv | 2.7600 |
C8B···H1E | 2.8400 | H14F···C1Axviii | 3.0800 |
C8C···H1G | 2.7700 | H14F···O1Axviii | 2.5400 |
C8C···H1H | 2.8400 | H14G···H11F | 2.1000 |
C8D···H1J | 2.8000 | H14G···H11E | 2.2500 |
C8D···H1K | 2.8200 | H14G···C11C | 2.3900 |
C9A···H14Iiv | 3.0800 | H14I···C9Axi | 3.0800 |
C9B···H14Ev | 2.8700 | H14I···C8Axi | 2.8700 |
C9C···H13Lxv | 2.9600 | H14I···H13H | 2.4200 |
C11A···H14A | 2.3900 | H14I···C6Bvii | 2.9600 |
C11B···H14D | 2.3900 | H14J···C11D | 2.4400 |
C11C···H14G | 2.3900 | H14J···H11G | 2.3200 |
C11D···H14J | 2.4400 | H14J···H11H | 2.1500 |
C12A···H4Dxvi | 3.0700 | H14K···H13K | 2.4000 |
C12A···H1Kiv | 3.0200 | H14L···H13K | 2.5900 |
C12A···H1Cvi | 2.98 (3) | H14L···C6Axii | 2.7500 |
C12B···H1L | 2.95 (3) | H14L···C7Axii | 3.0100 |
C12B···H4Axii | 3.0900 | ||
C1A—O1A—H1C | 101.0 (19) | N1B—C13B—H13F | 109.00 |
C1B—O1B—H1F | 104 (3) | N1B—C13B—H13D | 109.00 |
C1C—O1C—H1I | 99 (2) | H14D—C14B—H14E | 109.00 |
C1D—O1D—H1L | 105 (2) | H14D—C14B—H14F | 109.00 |
C12A—N1A—C14A | 124.3 (2) | H14E—C14B—H14F | 110.00 |
C13A—N1A—C14A | 115.8 (2) | N1B—C14B—H14D | 109.00 |
C12A—N1A—C13A | 119.8 (2) | N1B—C14B—H14F | 109.00 |
C12B—N1B—C13B | 119.8 (2) | N1B—C14B—H14E | 110.00 |
C13B—N1B—C14B | 116.0 (2) | O1C—C1C—C2C | 111.2 (2) |
C12B—N1B—C14B | 124.2 (2) | C1C—C2C—C7C | 119.1 (2) |
C13C—N1C—C14C | 115.9 (2) | C3C—C2C—C7C | 118.4 (2) |
C12C—N1C—C13C | 119.7 (2) | C1C—C2C—C3C | 122.5 (2) |
C12C—N1C—C14C | 124.4 (2) | C2C—C3C—C4C | 121.4 (2) |
C12D—N1D—C14D | 124.0 (2) | C3C—C4C—C5C | 120.3 (2) |
C13D—N1D—C14D | 116.4 (2) | C4C—C5C—C6C | 119.0 (2) |
C12D—N1D—C13D | 119.5 (2) | C5C—C6C—C7C | 121.7 (2) |
O1A—C1A—C2A | 111.08 (19) | C2C—C7C—C6C | 119.3 (2) |
C1A—C2A—C3A | 121.7 (2) | C2C—C7C—C8C | 120.6 (2) |
C1A—C2A—C7A | 119.4 (2) | C6C—C7C—C8C | 120.1 (2) |
C3A—C2A—C7A | 118.8 (2) | C7C—C8C—C9C | 174.8 (3) |
C2A—C3A—C4A | 120.8 (2) | C8C—C9C—C10C | 178.9 (3) |
C3A—C4A—C5A | 121.0 (2) | C9C—C10C—C11C | 112.2 (2) |
C4A—C5A—C6A | 118.7 (2) | C10C—C11C—C12C | 112.3 (2) |
C5A—C6A—C7A | 121.0 (2) | O2C—C12C—C11C | 119.8 (2) |
C2A—C7A—C8A | 121.8 (2) | N1C—C12C—C11C | 118.2 (2) |
C6A—C7A—C8A | 118.6 (2) | O2C—C12C—N1C | 122.0 (2) |
C2A—C7A—C6A | 119.6 (2) | O1C—C1C—H1H | 109.00 |
C7A—C8A—C9A | 174.6 (3) | C2C—C1C—H1G | 109.00 |
C8A—C9A—C10A | 177.9 (2) | O1C—C1C—H1G | 109.00 |
C9A—C10A—C11A | 112.5 (2) | C2C—C1C—H1H | 109.00 |
C10A—C11A—C12A | 112.4 (2) | H1G—C1C—H1H | 108.00 |
O2A—C12A—N1A | 121.6 (2) | C2C—C3C—H3C | 119.00 |
O2A—C12A—C11A | 120.1 (2) | C4C—C3C—H3C | 119.00 |
N1A—C12A—C11A | 118.4 (2) | C3C—C4C—H4C | 120.00 |
C2A—C1A—H1A | 109.00 | C5C—C4C—H4C | 120.00 |
C2A—C1A—H1B | 109.00 | C4C—C5C—H5C | 120.00 |
O1A—C1A—H1B | 109.00 | C6C—C5C—H5C | 121.00 |
H1A—C1A—H1B | 108.00 | C7C—C6C—H6C | 119.00 |
O1A—C1A—H1A | 109.00 | C5C—C6C—H6C | 119.00 |
C2A—C3A—H3A | 120.00 | C11C—C10C—H10F | 109.00 |
C4A—C3A—H3A | 120.00 | H10E—C10C—H10F | 108.00 |
C5A—C4A—H4A | 119.00 | C11C—C10C—H10E | 109.00 |
C3A—C4A—H4A | 120.00 | C9C—C10C—H10E | 109.00 |
C6A—C5A—H5A | 121.00 | C9C—C10C—H10F | 109.00 |
C4A—C5A—H5A | 121.00 | C10C—C11C—H11F | 109.00 |
C7A—C6A—H6A | 119.00 | H11E—C11C—H11F | 108.00 |
C5A—C6A—H6A | 120.00 | C10C—C11C—H11E | 109.00 |
C9A—C10A—H10A | 109.00 | C12C—C11C—H11F | 109.00 |
C9A—C10A—H10B | 109.00 | C12C—C11C—H11E | 109.00 |
H10A—C10A—H10B | 108.00 | N1C—C13C—H13H | 109.00 |
C11A—C10A—H10B | 109.00 | H13G—C13C—H13I | 109.00 |
C11A—C10A—H10A | 109.00 | H13G—C13C—H13H | 110.00 |
H11A—C11A—H11B | 108.00 | N1C—C13C—H13G | 109.00 |
C12A—C11A—H11B | 109.00 | N1C—C13C—H13I | 109.00 |
C12A—C11A—H11A | 109.00 | H13H—C13C—H13I | 109.00 |
C10A—C11A—H11A | 109.00 | H14G—C14C—H14I | 110.00 |
C10A—C11A—H11B | 109.00 | N1C—C14C—H14I | 110.00 |
H13A—C13A—H13C | 110.00 | H14G—C14C—H14H | 109.00 |
H13B—C13A—H13C | 109.00 | N1C—C14C—H14G | 109.00 |
H13A—C13A—H13B | 109.00 | N1C—C14C—H14H | 109.00 |
N1A—C13A—H13B | 109.00 | H14H—C14C—H14I | 110.00 |
N1A—C13A—H13C | 109.00 | O1D—C1D—C2D | 110.47 (19) |
N1A—C13A—H13A | 109.00 | C1D—C2D—C3D | 122.1 (2) |
H14A—C14A—H14B | 109.00 | C1D—C2D—C7D | 119.4 (2) |
H14B—C14A—H14C | 109.00 | C3D—C2D—C7D | 118.4 (2) |
H14A—C14A—H14C | 110.00 | C2D—C3D—C4D | 121.0 (2) |
N1A—C14A—H14B | 109.00 | C3D—C4D—C5D | 120.4 (2) |
N1A—C14A—H14A | 110.00 | C4D—C5D—C6D | 119.4 (2) |
N1A—C14A—H14C | 110.00 | C5D—C6D—C7D | 121.1 (2) |
O1B—C1B—C2B | 111.7 (2) | C2D—C7D—C8D | 120.7 (2) |
C1B—C2B—C3B | 122.5 (2) | C6D—C7D—C8D | 119.8 (2) |
C3B—C2B—C7B | 118.8 (2) | C2D—C7D—C6D | 119.5 (2) |
C1B—C2B—C7B | 118.7 (2) | C7D—C8D—C9D | 175.9 (3) |
C2B—C3B—C4B | 120.7 (2) | C8D—C9D—C10D | 177.7 (3) |
C3B—C4B—C5B | 120.5 (2) | C9D—C10D—C11D | 112.3 (2) |
C4B—C5B—C6B | 119.1 (2) | C10D—C11D—C12D | 111.7 (2) |
C5B—C6B—C7B | 121.2 (2) | O2D—C12D—C11D | 120.4 (2) |
C6B—C7B—C8B | 119.6 (2) | N1D—C12D—C11D | 118.6 (2) |
C2B—C7B—C8B | 120.8 (2) | O2D—C12D—N1D | 121.0 (2) |
C2B—C7B—C6B | 119.7 (2) | O1D—C1D—H1J | 110.00 |
C7B—C8B—C9B | 175.6 (3) | O1D—C1D—H1K | 110.00 |
C8B—C9B—C10B | 177.6 (3) | C2D—C1D—H1J | 110.00 |
C9B—C10B—C11B | 111.7 (2) | C2D—C1D—H1K | 109.00 |
C10B—C11B—C12B | 111.9 (2) | H1J—C1D—H1K | 108.00 |
O2B—C12B—C11B | 120.2 (2) | C2D—C3D—H3D | 119.00 |
N1B—C12B—C11B | 118.0 (2) | C4D—C3D—H3D | 119.00 |
O2B—C12B—N1B | 121.8 (2) | C3D—C4D—H4D | 120.00 |
C2B—C1B—H1D | 109.00 | C5D—C4D—H4D | 120.00 |
O1B—C1B—H1E | 109.00 | C4D—C5D—H5D | 120.00 |
C2B—C1B—H1E | 109.00 | C6D—C5D—H5D | 120.00 |
O1B—C1B—H1D | 109.00 | C5D—C6D—H6D | 119.00 |
H1D—C1B—H1E | 108.00 | C7D—C6D—H6D | 120.00 |
C4B—C3B—H3B | 120.00 | C9D—C10D—H10G | 109.00 |
C2B—C3B—H3B | 120.00 | C9D—C10D—H10H | 109.00 |
C3B—C4B—H4B | 120.00 | C11D—C10D—H10G | 109.00 |
C5B—C4B—H4B | 120.00 | C11D—C10D—H10H | 109.00 |
C6B—C5B—H5B | 120.00 | H10G—C10D—H10H | 108.00 |
C4B—C5B—H5B | 121.00 | C10D—C11D—H11G | 109.00 |
C5B—C6B—H6B | 119.00 | C10D—C11D—H11H | 109.00 |
C7B—C6B—H6B | 119.00 | C12D—C11D—H11G | 109.00 |
H10C—C10B—H10D | 108.00 | C12D—C11D—H11H | 109.00 |
C9B—C10B—H10C | 109.00 | H11G—C11D—H11H | 108.00 |
C11B—C10B—H10C | 109.00 | N1D—C13D—H13J | 110.00 |
C11B—C10B—H10D | 109.00 | N1D—C13D—H13K | 109.00 |
C9B—C10B—H10D | 109.00 | N1D—C13D—H13L | 109.00 |
C10B—C11B—H11C | 109.00 | H13J—C13D—H13K | 109.00 |
H11C—C11B—H11D | 108.00 | H13J—C13D—H13L | 109.00 |
C12B—C11B—H11C | 109.00 | H13K—C13D—H13L | 109.00 |
C12B—C11B—H11D | 109.00 | N1D—C14D—H14J | 110.00 |
C10B—C11B—H11D | 109.00 | N1D—C14D—H14K | 109.00 |
H13D—C13B—H13E | 110.00 | N1D—C14D—H14L | 109.00 |
H13E—C13B—H13F | 109.00 | H14J—C14D—H14K | 110.00 |
H13D—C13B—H13F | 110.00 | H14J—C14D—H14L | 109.00 |
N1B—C13B—H13E | 110.00 | H14K—C14D—H14L | 109.00 |
C13A—N1A—C12A—C11A | −179.5 (2) | C2B—C3B—C4B—C5B | −0.3 (4) |
C13A—N1A—C12A—O2A | −0.5 (4) | C3B—C4B—C5B—C6B | −0.3 (4) |
C14A—N1A—C12A—C11A | −3.1 (3) | C4B—C5B—C6B—C7B | 0.2 (4) |
C14A—N1A—C12A—O2A | 175.9 (2) | C5B—C6B—C7B—C8B | −178.8 (2) |
C14B—N1B—C12B—C11B | −0.1 (4) | C5B—C6B—C7B—C2B | 0.5 (4) |
C13B—N1B—C12B—C11B | 179.2 (2) | C9B—C10B—C11B—C12B | 173.9 (2) |
C14B—N1B—C12B—O2B | −179.4 (2) | C10B—C11B—C12B—N1B | 177.8 (2) |
C13B—N1B—C12B—O2B | −0.1 (4) | C10B—C11B—C12B—O2B | −2.9 (3) |
C13C—N1C—C12C—O2C | −1.2 (4) | O1C—C1C—C2C—C7C | 179.3 (2) |
C14C—N1C—C12C—C11C | 0.2 (4) | O1C—C1C—C2C—C3C | 1.9 (4) |
C14C—N1C—C12C—O2C | 179.2 (2) | C1C—C2C—C7C—C8C | 7.0 (4) |
C13C—N1C—C12C—C11C | 179.8 (2) | C1C—C2C—C7C—C6C | −176.2 (2) |
C13D—N1D—C12D—O2D | −3.3 (4) | C1C—C2C—C3C—C4C | 177.1 (3) |
C14D—N1D—C12D—C11D | 0.7 (4) | C3C—C2C—C7C—C6C | 1.4 (4) |
C13D—N1D—C12D—C11D | 177.1 (2) | C3C—C2C—C7C—C8C | −175.5 (2) |
C14D—N1D—C12D—O2D | −179.7 (2) | C7C—C2C—C3C—C4C | −0.4 (4) |
O1A—C1A—C2A—C7A | 179.9 (2) | C2C—C3C—C4C—C5C | −0.9 (4) |
O1A—C1A—C2A—C3A | 2.6 (3) | C3C—C4C—C5C—C6C | 1.1 (4) |
C7A—C2A—C3A—C4A | −0.8 (4) | C4C—C5C—C6C—C7C | −0.1 (4) |
C1A—C2A—C7A—C6A | −176.2 (2) | C5C—C6C—C7C—C8C | 175.7 (3) |
C3A—C2A—C7A—C8A | −179.2 (2) | C5C—C6C—C7C—C2C | −1.2 (4) |
C1A—C2A—C3A—C4A | 176.6 (2) | C9C—C10C—C11C—C12C | −177.4 (2) |
C3A—C2A—C7A—C6A | 1.2 (4) | C10C—C11C—C12C—O2C | 7.1 (3) |
C1A—C2A—C7A—C8A | 3.4 (4) | C10C—C11C—C12C—N1C | −173.9 (2) |
C2A—C3A—C4A—C5A | −0.7 (4) | O1D—C1D—C2D—C3D | 0.4 (3) |
C3A—C4A—C5A—C6A | 1.6 (4) | O1D—C1D—C2D—C7D | 178.1 (2) |
C4A—C5A—C6A—C7A | −1.2 (4) | C1D—C2D—C3D—C4D | 175.1 (2) |
C5A—C6A—C7A—C2A | −0.2 (4) | C7D—C2D—C3D—C4D | −2.6 (3) |
C5A—C6A—C7A—C8A | −179.9 (2) | C1D—C2D—C7D—C6D | −175.3 (2) |
C9A—C10A—C11A—C12A | −175.15 (19) | C1D—C2D—C7D—C8D | 5.7 (3) |
C10A—C11A—C12A—N1A | −176.1 (2) | C3D—C2D—C7D—C6D | 2.4 (3) |
C10A—C11A—C12A—O2A | 4.9 (3) | C3D—C2D—C7D—C8D | −176.5 (2) |
O1B—C1B—C2B—C7B | −174.4 (2) | C2D—C3D—C4D—C5D | 1.0 (4) |
O1B—C1B—C2B—C3B | 3.9 (4) | C3D—C4D—C5D—C6D | 0.7 (4) |
C3B—C2B—C7B—C8B | 178.2 (2) | C4D—C5D—C6D—C7D | −0.8 (4) |
C1B—C2B—C3B—C4B | −177.3 (2) | C5D—C6D—C7D—C2D | −0.8 (4) |
C1B—C2B—C7B—C8B | −3.4 (3) | C5D—C6D—C7D—C8D | 178.2 (2) |
C1B—C2B—C7B—C6B | 177.3 (2) | C9D—C10D—C11D—C12D | 179.2 (2) |
C3B—C2B—C7B—C6B | −1.1 (3) | C10D—C11D—C12D—O2D | 12.4 (3) |
C7B—C2B—C3B—C4B | 1.0 (4) | C10D—C11D—C12D—N1D | −168.1 (2) |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) x+1/2, −y, z; (iii) −x+1/2, y+1, z−1/2; (iv) −x+1/2, y, z−1/2; (v) x−1/2, −y+2, z; (vi) x−1/2, −y+1, z; (vii) x, y−1, z; (viii) −x+1/2, y−1, z−1/2; (ix) −x+1, −y+1, z−1/2; (x) x, y+1, z; (xi) −x+1/2, y, z+1/2; (xii) −x+1/2, y+1, z+1/2; (xiii) x−1/2, −y, z; (xiv) x+1/2, −y+2, z; (xv) −x+1, −y+2, z−1/2; (xvi) −x, −y+1, z−1/2; (xvii) −x, −y+2, z−1/2; (xviii) −x+1, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1C···O2Ai | 0.80 (3) | 1.96 (3) | 2.757 (3) | 173 (3) |
O1B—H1F···O2Div | 0.84 (4) | 1.92 (4) | 2.747 (3) | 170 (3) |
O1C—H1I···O2Cvi | 0.80 (3) | 1.96 (3) | 2.759 (3) | 173 (3) |
O1D—H1L···O2B | 0.80 (3) | 1.92 (3) | 2.718 (3) | 173 (3) |
C3A—H3A···O1A | 0.95 | 2.40 | 2.752 (3) | 102 |
C3B—H3B···O1B | 0.95 | 2.43 | 2.771 (3) | 101 |
C3C—H3C···O1C | 0.95 | 2.41 | 2.761 (3) | 101 |
C3D—H3D···O1D | 0.95 | 2.38 | 2.736 (3) | 101 |
C5A—H5A···O1Axiii | 0.95 | 2.48 | 3.380 (3) | 158 |
C5B—H5B···O1Dx | 0.95 | 2.38 | 3.293 (3) | 161 |
C5C—H5C···O1Cxiv | 0.95 | 2.39 | 3.338 (3) | 173 |
C5D—H5D···O1Bxix | 0.95 | 2.50 | 3.397 (3) | 157 |
C13A—H13A···O2A | 0.98 | 2.36 | 2.723 (3) | 101 |
C13A—H13C···O2Dxvii | 0.98 | 2.59 | 3.544 (3) | 163 |
C13B—H13D···O2Axi | 0.98 | 2.56 | 3.525 (4) | 169 |
C13C—H13I···O2Bi | 0.98 | 2.54 | 3.507 (3) | 169 |
C14B—H14F···O1Axviii | 0.98 | 2.54 | 3.466 (4) | 157 |
C14C—H14H···O1Di | 0.98 | 2.48 | 3.391 (4) | 155 |
Symmetry codes: (i) x+1/2, −y+1, z; (iv) −x+1/2, y, z−1/2; (vi) x−1/2, −y+1, z; (x) x, y+1, z; (xi) −x+1/2, y, z+1/2; (xiii) x−1/2, −y, z; (xiv) x+1/2, −y+2, z; (xvii) −x, −y+2, z−1/2; (xviii) −x+1, −y+1, z+1/2; (xix) −x+1/2, y−1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H17NO2 |
Mr | 231.29 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 161 |
a, b, c (Å) | 14.166 (2), 12.9093 (14), 27.669 (5) |
V (Å3) | 5060.1 (14) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.36 × 0.30 |
Data collection | |
Diffractometer | Siemens SMART 1K CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 57442, 6075, 4295 |
Rint | 0.088 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.088, 1.06 |
No. of reflections | 6075 |
No. of parameters | 637 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.23 |
Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1996), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1C···O2Ai | 0.80 (3) | 1.96 (3) | 2.757 (3) | 173 (3) |
O1B—H1F···O2Dii | 0.84 (4) | 1.92 (4) | 2.747 (3) | 170 (3) |
O1C—H1I···O2Ciii | 0.80 (3) | 1.96 (3) | 2.759 (3) | 173 (3) |
O1D—H1L···O2B | 0.80 (3) | 1.92 (3) | 2.718 (3) | 173 (3) |
Symmetry codes: (i) x+1/2, −y+1, z; (ii) −x+1/2, y, z−1/2; (iii) x−1/2, −y+1, z. |
The title compound, (I), was prepared for an investigation of the addition of nucleophiles to C≡C triple bonds and C—H activation in the benzylic position by homogeneous gold catalysts (Hashmi, 2004).
Compound (I) crystallizes with four independent molecules (A, B, C and D) per asymmetric unit. The molecular structure of molecule A is illustrated in Fig. 1. The dimensions of all four molecules are very similar. The amide groups are planar; the O2—C12—N1—C14 torsion angles are 175.9 (2), -179.4 (2), 179.2 (2) and -179.7 (2)° for molecules A, B, C and D, respectively. The N atoms show no significant deviations from planarity; the sum of the three valence angles about the N atoms are 359.9 (2), 360.0 (2), 360.0 (2) and 359.9 (2)° for N1A, N1B, N1C and N1D, respectively. The angles between the plane of the phenyl group and the plane of the N,N-dimethylamide group are 77.2 (1), 82.2 (1), 80.2 (1) and 74.6 (1)° for molecules A, B, C and D, respectively. This confirms the similarity of the four molecules.
The C1—O1 bond is coplanar with the phenyl ring; the torsion angles O1—C1—C2—C3 are 2.6 (3), 3.9 (4), 1.9 (4) and 0.4 (3)° for molecules A, B, C and D, respectively. This conformation results in contact distances between atoms O1 and H3 of 2.40, 2.43, 2.41 and 2.38 Å, for molecules A, B, C and D, respectively.
In the crystal structure the molecules are connected by intermolecular hydrogen bonds between the hydroxyl groups and the keto groups to form chains. Details of the hydrogen bonding are given in Table 1, and the crystal packing is illustrated in Figs. 2 and 3. Molecules A and C are hydrogen bonded to their symmetry-related molecules to form chains extending in the a direction (Fig. 2). Molecules in these chains are related by an a-glide plane. Molecules B and D are hydrogen bonded to one another and form alternating zigzag chains running in the c direction (Fig. 3). The hydrogen-bonded chains are connected by intermolecular C—H···π and C—H···O contacts. The crystal packing shows a number of intermolecular C—H···O interactions with H···O distances between 2.36 and 2.59 Å and five weak intermolecular Cmethylene—H···πphenyl interactions.
Each of the hydrogen-bonded motifs shows pseudo-symmetry. Molecules A and C are related by the pseudo-relationship xC≈ 0.60 - xA, yC≈ 1.02 - yA and zC≈ 1/4 + zA. This is a pseudo-twofold screw axis about (0.30, 0.51, z) with a translation of c/4. Thus molecule C and molecule A at (-x, -y, 1/2 + z) are related by a pseudo-translation vector (0.60, 1.02, -0.25). The coordinates of molecules B and D also show a pseudo-relationship: xD ≈ xB - 0.11, yD≈ 2.02 - yB and zD≈ 1/4 + zB. This is a pseudo-glide plane perpendicular to the b axis through y = 1.01 with an unusual translation vector of (-0.11, 0, 1/4). Thus molecule D and molecule B, at (1/2 + x, -y, z), are related by a pseudo-translation vector (-0.61, 2.02, 1/4). This shows the pseudo-symmetry between the AC and BD structures to be very similar.