5-[2-(Hydroxy­meth­yl)phen­yl]-N,N-dimethyl­pent-4-ynamide

The title compound, C₁₄H₁₇NO₂, crystallizes with four independent mol­ecules (A, B, C and D) in the asymmetric unit. In the crystal structure, mol­ecules A and C are hydrogen bonded to their symmetry-related mol­ecules to form parallel chains extending in the a direction. Mol­ecules B and D are hydrogen bonded to one another and form alternating zigzag chains running in the c direction. These hydrogen-bonded chains are connected via inter­molecular C—H...π and C—H...O contacts. The four independent mol­ecules are related by non-crystallographic pseudo-symmetry.

Key indicators

• Single-crystal X-ray study
• T = 161 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.088
• Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7B    -   C8B     ..       5.16 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7D    -   C8D     ..       5.65 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7A    -   C8A    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7B    -   C8B    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7C    -   C8C    ...       1.45 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C7D    -   C8D    ...       1.44 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C14 H17 N O2

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           28.20
           From the CIF: _reflns_number_total               6075
           Count of symmetry unique reflns         6366
           Completeness (_total/calc)             95.43%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

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 C_methylene—H···π_phenyl interactions.

Each of the hydrogen-bonded motifs shows pseudo-symmetry. Molecules A and C are related by the pseudo-relationship x_C≈ 0.60 - x_A, y_C≈ 1.02 - y_A and z_C≈ 1/4 + z_A. 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: x_D ≈ x_B - 0.11, y_D≈ 2.02 - y_B and z_D≈ 1/4 + z_B. 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.

S2. Experimental

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).

S3. Refinement

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, C_secondary—H = 0.99 Å, with U_iso(H) = 1.2U_eq(parent C atom), and C_methyl—H = 0.98 Å, with U_iso(H) = 1.5U_eq(parent C_methyl atom). The hydroxyl H atoms were located in difference Fourier maps and refined isotropically [O—H = 0.80 (3) - 0.84 (4) Å].

Computing details

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.

Figures

	Fig. 1. The molecular structure of molecule A of compound (I), showing the numbering scheme and displacement ellipsoids drawn at the 50% probability level. Molecules B, C and D are very similar.
	Fig. 2. A perspective view down the b axis of the crystal packing of compound (I), showing only the hydrogen-bonded chains of molecules A and C. Hydrogen bonds are shown as dashed lines and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. A perspective view down the b axis of the crystal packing of compound (I), showing only the hydroge-bonded chains of molecules B and D. Hydrogen bonds are shown as dashed lines and displacement ellipsoids are drawn at the 50% probability level.

5-[2-(Hydroxymethyl)phenyl]-N,N-dimethylpent-4-ynamide

Crystal data

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) Å^3	Block, colorless
Z = 16	0.50 × 0.36 × 0.30 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.04P)^2] where P = (Fo^2 + 2Fc^2)/3
6075 reflections	(Δ/σ)max = 0.001
637 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.23 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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···O2A^i	2.757 (3)	C12C···H4B^xiv	3.0400
O1A···C5A^ii	3.380 (3)	C12C···H1I^i	3.00 (3)
O1B···C5D^iii	3.397 (3)	C12D···H1B^xii	3.0900
O1B···O2D^iv	2.747 (3)	C14A···H11A	2.8300
O1C···C5C^v	3.338 (3)	C14A···H11B	2.7700
O1C···O2C^vi	2.759 (3)	C14B···H11C	2.7700
O1D···C14C^vi	3.391 (4)	C14B···H11D	2.8200
O1D···O2B	2.718 (3)	C14C···H11E	2.8700
O1D···C5B^vii	3.293 (3)	C14C···H11F	2.7200
O2A···O1A^vi	2.757 (3)	C14D···H11G	2.9600
O2A···C1A^vi	3.383 (3)	C14D···H11H	2.6600
O2B···O1D	2.718 (3)	H1A···C8A	2.8100
O2C···C14A^i	3.374 (3)	H1A···H6B^viii	2.4800
O2C···C1C^i	3.382 (3)	H1B···C8A	2.8500
O2C···O1C^i	2.759 (3)	H1B···C12D^viii	3.0900
O1A···H3A	2.4000	H1B···H4D^iv	2.3500
O1A···H10H^viii	2.6700	H1B···O2D^viii	2.8400
O1A···H14F^ix	2.5400	H1C···C12A^i	2.98 (3)
O1A···H5A^ii	2.4800	H1C···O2A^i	1.96 (3)
O1B···H5D^iii	2.5000	H1D···C8B	2.7400
O1B···H3B	2.4300	H1D···H4C	2.3400
O1B···H13L^iv	2.8900	H1E···C8B	2.8400
O1B···H10F^x	2.7500	H1F···H5D^iii	2.5300
O1C···H5C^v	2.3900	H1F···O2D^iv	1.92 (4)
O1C···H3C	2.4100	H1F···C13D^iv	3.03 (3)
O1D···H14H^vi	2.4800	H1F···C12D^iv	2.91 (4)
O1D···H10B^xi	2.6900	H1G···C8C	2.7700
O1D···H5B^vii	2.3800	H1G···H6D^iv	2.3500
O1D···H3D	2.3800	H1H···H4B^vii	2.2800
O2A···H13D^iv	2.5600	H1H···C8C	2.8400
O2A···H1C^vi	1.96 (3)	H1H···O2B	2.8900
O2A···H10B	2.7400	H1I···O2C^vi	1.96 (3)
O2A···H13A	2.3600	H1I···C12C^vi	3.00 (3)
O2A···H1K^iv	2.7800	H1I···H5C^v	2.5700
O2A···H10A	2.5600	H1J···C8D	2.8000
O2B···H13F	2.3900	H1K···O2A^xi	2.7800
O2B···H10C	2.7400	H1K···C8D	2.8200
O2B···H10D	2.5500	H1K···C12A^xi	3.0200
O2B···H1H	2.8900	H1K···H4A^xii	2.3300
O2B···H1L	1.92 (3)	H1L···C12B	2.95 (3)
O2B···H13I^vi	2.5400	H1L···O2B	1.92 (3)
O2C···H14B^i	2.8400	H3A···O1A	2.4000
O2C···H10E	2.5800	H3B···O1B	2.4300
O2C···H1I^i	1.96 (3)	H3C···O1C	2.4100
O2C···H13G	2.4200	H3D···O1D	2.3800
O2C···H10F	2.7200	H4A···C12B^viii	3.0900
O2D···H10H	2.7100	H4A···H1K^viii	2.3300
O2D···H13J	2.5000	H4B···C12C^v	3.0400
O2D···H13L	2.8800	H4B···H1H^x	2.2800
O2D···H10G	2.5900	H4C···H1D	2.3400
O2D···H1B^xii	2.8400	H4D···H1B^xi	2.3500
C1A···O2A^i	3.383 (3)	H4D···C1A^xi	3.0700
C1B···O2D^iv	3.263 (3)	H5A···O1A^xiii	2.4800
C1C···O2C^vi	3.382 (3)	H5B···O1D^x	2.3800
C2B···C11C^x	3.588 (3)	H5C···H1I^xiv	2.5700
C2C···C11B	3.564 (4)	H5C···O1C^xiv	2.3900
C2D···C11A^xi	3.485 (3)	H6A···H1J^xvi	2.3400
C3A···C11D^viii	3.563 (4)	H6B···H1A^xii	2.4800
C3A···C10D^viii	3.538 (4)	H10A···O2A	2.5600
C3B···C11C^x	3.513 (3)	H10B···C3D^iv	2.9100
C3B···C10C^x	3.551 (3)	H10B···O2A	2.7400
C3C···C11B	3.561 (4)	H10B···O1D^iv	2.6900
C3C···C10B	3.534 (4)	H10B···C1D^iv	3.0700
C3D···C11A^xi	3.493 (3)	H10C···O2B	2.7400
C3D···C10A^xi	3.463 (3)	H10C···C3C	2.9600
C4A···C11B^viii	3.500 (4)	H10D···O2B	2.5500
C4A···C12B^viii	3.562 (3)	H10E···O2C	2.5800
C4B···C12C^v	3.428 (3)	H10E···C3B^xiv	3.0300
C4B···C11C^v	3.451 (3)	H10F···C3B^vii	3.0500
C5A···O1A^xiii	3.380 (3)	H10F···O2C	2.7200
C5B···O1D^x	3.293 (3)	H10F···O1B^vii	2.7500
C5C···O1C^xiv	3.338 (3)	H10G···O2D	2.5900
C6A···C14D^viii	3.598 (4)	H10H···O1A^xii	2.6700
C6B···C14C^x	3.585 (4)	H10H···C1A^xii	3.0800
C6C···C14D^xv	3.492 (4)	H10H···O2D	2.7100
C7C···C14D^xv	3.545 (4)	H10H···C3A^xii	2.9900
C8A···C14C^iv	3.573 (4)	H11A···C5D^xvi	2.8100
C8B···C14B^v	3.507 (4)	H11A···C14A	2.8300
C9A···C14C^iv	3.567 (4)	H11A···H13K^viii	2.4700
C9B···C14B^v	3.396 (4)	H11A···H14A	2.2000
C10A···C3D^iv	3.463 (3)	H11A···C4D^xvi	2.8300
C10B···C3C	3.534 (4)	H11B···C7D^iv	3.0800
C10C···C3B^vii	3.551 (3)	H11B···C2D^iv	2.8500
C10D···C3A^xii	3.538 (4)	H11B···C5D^iv	3.1000
C11A···C3D^iv	3.493 (3)	H11B···C14A	2.7700
C11A···C2D^iv	3.485 (3)	H11B···H14A	2.1600
C11A···C4D^xvi	3.446 (3)	H11B···C3D^iv	2.7700
C11B···C2C	3.564 (4)	H11B···C4D^iv	2.9000
C11B···C3C	3.561 (4)	H11C···C14B	2.7700
C11B···C4A^xii	3.500 (4)	H11C···H14D	2.1200
C11C···C4B^xiv	3.451 (3)	H11C···C2C	2.9300
C11C···C3B^vii	3.513 (3)	H11C···C7C	3.0700
C11C···C2B^vii	3.588 (3)	H11C···C4C	2.9100
C11D···C3A^xii	3.563 (4)	H11C···C5C	3.0300
C12B···C4A^xii	3.562 (3)	H11C···C3C	2.8400
C12C···C4B^xiv	3.428 (3)	H11C···C6C	3.1000
C14A···O2C^vi	3.374 (3)	H11D···H13H^x	2.5900
C14B···C9B^xiv	3.396 (4)	H11D···C14B	2.8200
C14B···C8B^xiv	3.507 (4)	H11D···C5A^xii	2.8900
C14C···C9A^xi	3.567 (4)	H11D···H14D	2.2300
C14C···C6B^vii	3.585 (4)	H11D···C4A^xii	2.8800
C14C···C8A^xi	3.573 (4)	H11E···C4B^xiv	2.8100
C14D···C6A^xii	3.598 (4)	H11E···C14C	2.8700
C1A···H10H^viii	3.0800	H11E···H14G	2.2500
C1A···H14F^ix	3.0800	H11E···C5B^xiv	2.9300
C1A···H4D^iv	3.0700	H11F···H14G	2.1000
C1D···H10B^xi	3.0700	H11F···C14C	2.7200
C1D···H14H^vi	3.1000	H11F···C2B^vii	2.9400
C2A···H11H^viii	3.0900	H11F···C3B^vii	2.7600
C2B···H11F^x	2.9400	H11F···C4B^vii	2.8800
C2C···H14K^xv	3.1000	H11G···H14J	2.3200
C2C···H11C	2.9300	H11G···H13B^xi	2.5900
C2D···H11B^xi	2.8500	H11G···C14D	2.9600
C3A···H10H^viii	2.9900	H11H···H14J	2.1500
C3A···H11H^viii	2.8800	H11H···C14D	2.6600
C3B···H10E^v	3.0300	H11H···C3A^xii	2.8800
C3B···H10F^x	3.0500	H11H···C4A^xii	3.0100
C3B···H11F^x	2.7600	H11H···C2A^xii	3.0900
C3C···H10C	2.9600	H13A···O2A	2.3600
C3C···H10G^iv	2.8500	H13B···H11G^iv	2.5900
C3C···H11C	2.8400	H13B···H14C	2.4400
C3D···H10B^xi	2.9100	H13C···O2D^xvii	2.5900
C3D···H11B^xi	2.7700	H13C···H10G^xvii	2.5500
C4A···H11D^viii	2.8800	H13C···C10D^xvii	3.0700
C4A···H11H^viii	3.0100	H13D···O2A^xi	2.5600
C4B···H11F^x	2.8800	H13E···H14E	2.3700
C4B···H11E^v	2.8100	H13F···O2B	2.3900
C4C···H10G^iv	3.0300	H13G···O2C	2.4200
C4C···H11C	2.9100	H13H···H11D^vii	2.5900
C4D···H11B^xi	2.9000	H13H···H14I	2.4200
C5A···H11D^viii	2.8900	H13J···O2D	2.5000
C5B···H11E^v	2.9300	H13K···H11A^xii	2.4700
C5C···H11C	3.0300	H13K···H14L	2.5900
C5D···H11B^xi	3.1000	H13K···H14K	2.4000
C6A···H14L^viii	2.7500	H13L···O2D	2.8800
C6B···H14I^x	2.9600	H14A···H11B	2.1600
C6C···H11C	3.1000	H14A···H11A	2.2000
C7A···H14L^viii	3.0100	H14A···C11A	2.3900
C7C···H14K^xv	2.8200	H14B···O2C^vi	2.8400
C7C···H11C	3.0700	H14C···H13B	2.4400
C7D···H11B^xi	3.0800	H14D···C11B	2.3900
C8A···H14I^iv	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···C9B^xiv	2.8700
C8B···H14E^v	2.7600	H14E···C8B^xiv	2.7600
C8B···H1E	2.8400	H14F···C1A^xviii	3.0800
C8C···H1G	2.7700	H14F···O1A^xviii	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···H14I^iv	3.0800	H14I···C9A^xi	3.0800
C9B···H14E^v	2.8700	H14I···C8A^xi	2.8700
C9C···H13L^xv	2.9600	H14I···H13H	2.4200
C11A···H14A	2.3900	H14I···C6B^vii	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···H4D^xvi	3.0700	H14K···H13K	2.4000
C12A···H1K^iv	3.0200	H14L···H13K	2.5900
C12A···H1C^vi	2.98 (3)	H14L···C6A^xii	2.7500
C12B···H1L	2.95 (3)	H14L···C7A^xii	3.0100
C12B···H4A^xii	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.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1C···O2A^i	0.80 (3)	1.96 (3)	2.757 (3)	173 (3)
O1B—H1F···O2D^iv	0.84 (4)	1.92 (4)	2.747 (3)	170 (3)
O1C—H1I···O2C^vi	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···O1A^xiii	0.95	2.48	3.380 (3)	158
C5B—H5B···O1D^x	0.95	2.38	3.293 (3)	161
C5C—H5C···O1C^xiv	0.95	2.39	3.338 (3)	173
C5D—H5D···O1B^xix	0.95	2.50	3.397 (3)	157
C13A—H13A···O2A	0.98	2.36	2.723 (3)	101
C13A—H13C···O2D^xvii	0.98	2.59	3.544 (3)	163
C13B—H13D···O2A^xi	0.98	2.56	3.525 (4)	169
C13C—H13I···O2B^i	0.98	2.54	3.507 (3)	169
C14B—H14F···O1A^xviii	0.98	2.54	3.466 (4)	157
C14C—H14H···O1D^i	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.