N,N′-Bis(6-tert-butoxy­carbonyl­amino-2-pyridyl)­terephthal­amide di­methyl sulfoxide disolvate

Ohba, S.; Miyamoto, H.; Fujioka, A.; Ikeuchi, T.; Lehn, J.-M.

doi:10.1107/S1600536804033367

Buy article online - an online subscription or single-article purchase is required to access this article.

N,N′-Bis(6-tert-butoxycarbonylamino-2-pyridyl)terephthalamide dimethyl sulfoxide disolvate

S. Ohba, H. Miyamoto, A. Fujioka, T. Ikeuchi and J.-M. Lehn

In the title compound, C₂₈H₃₂N₆O₆·2C₂H₆OS, the host molecules are linked by N—H

N hydrogen bonds at both of the terminal amide groups, forming zigzag chains along the [01 $\overline 1$ ] direction. Two dimethyl sulfoxide molecules are connected to a host molecule by N—H

O hydrogen bonds.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804033367/tk6202sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804033367/tk6202Isup2.hkl Contains datablock I

CCDC reference: 247691

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.016 Å
R factor = 0.061
wR factor = 0.207
Data-to-parameter ratio = 11.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         16

Alert level C
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...       0.30
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.93 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O7     -   C27     ..       5.11 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C27    -   C28     ..       5.56 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C29
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C41
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         S2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C2 H6 O S

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               4775
           Count of symmetry unique reflns         4484
           Completeness (_total/calc)            106.49%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       291
           Fraction of Friedel pairs measured     0.065
           Are heavy atom types Z>Si present          yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: WinAFC Diffractometer Control Software (Rigaku, 1999); cell refinement: WinAFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: TEXSAN.

(I) top

Crystal data top

C₂₈H₃₂N₆O₆·2C₂H₆OS	F(000) = 1496
M_r = 704.85	D_x = 1.269 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2c -2n	Cell parameters from 30 reflections
a = 16.597 (3) Å	θ = 10.2–12.9°
b = 22.522 (3) Å	µ = 0.20 mm⁻¹
c = 9.871 (2) Å	T = 295 K
V = 3689.8 (11) Å³	Prismatic, colorless
Z = 4	0.5 × 0.3 × 0.2 mm

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.037
ω scans	θ_max = 27.5°
Absorption correction: integration (ABSCOR; Higashi, 1999)	h = −9→21
T_min = 0.921, T_max = 0.949	k = 0→29
5747 measured reflections	l = −12→5
4775 independent reflections	3 standard reflections every 150 reflections
1742 reflections with I > 2σ(I)	intensity decay: 7.4%

Refinement top

Refinement on F²	w = 1/[σ²(F_o²) + (0.0925P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.061	(Δ/σ)_max = 0.001
wR(F²) = 0.207	Δρ_max = 0.29 e Å⁻³
S = 0.95	Δρ_min = −0.23 e Å⁻³
4775 reflections	Absolute structure: (Flack, 1983), 291 Friedel pairs
433 parameters	Absolute structure parameter: 0.2 (3)
H-atom parameters constrained

Special details top

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.7854 (3)	0.2086 (2)	1.0807 (6)	0.154 (2)
S2	0.6556 (4)	−0.2043 (2)	1.0888 (6)	0.180 (2)
O3	0.7128 (6)	0.1759 (4)	1.0427 (10)	0.138 (4)
O4	0.7274 (7)	−0.1835 (4)	1.1584 (12)	0.161 (4)
O5	0.5162 (4)	0.3635 (3)	0.6478 (8)	0.073 (2)
O6	0.4998 (5)	0.3061 (3)	0.4631 (7)	0.084 (2)
O7	0.7059 (5)	0.0118 (3)	0.6999 (8)	0.078 (2)
O8	0.7988 (5)	−0.0093 (3)	1.4124 (7)	0.079 (2)
O9	0.9912 (4)	−0.3622 (3)	1.4904 (8)	0.072 (2)
O10	1.0180 (5)	−0.2984 (3)	1.6617 (9)	0.093 (3)
N11	0.5745 (5)	0.2765 (3)	0.6450 (8)	0.056 (2)
N12	0.6254 (4)	0.1869 (3)	0.7059 (7)	0.046 (2)
N13	0.6794 (4)	0.1002 (3)	0.7921 (8)	0.052 (2)
N14	0.8118 (4)	−0.1049 (3)	1.3371 (8)	0.048 (2)
N15	0.8777 (4)	−0.1860 (3)	1.4218 (8)	0.045 (2)
N16	0.9419 (5)	−0.2713 (3)	1.4809 (8)	0.056 (2)
C17	0.4566 (7)	0.4096 (5)	0.6059 (12)	0.070 (3)
C18	0.4621 (9)	0.4535 (5)	0.7194 (17)	0.129 (6)
C19	0.4831 (7)	0.4381 (5)	0.4763 (17)	0.113 (5)
C20	0.3748 (7)	0.3849 (5)	0.5979 (14)	0.090 (4)
C21	0.5264 (6)	0.3135 (5)	0.5687 (11)	0.056 (3)
C22	0.6016 (5)	0.2204 (4)	0.6051 (10)	0.049 (3)
C23	0.6075 (7)	0.2033 (4)	0.4714 (10)	0.071 (3)
C24	0.6367 (6)	0.1485 (5)	0.4423 (10)	0.069 (3)
C25	0.6619 (6)	0.1105 (5)	0.5461 (11)	0.062 (3)
C26	0.6554 (5)	0.1316 (4)	0.6753 (11)	0.044 (2)
C27	0.7012 (6)	0.0439 (5)	0.8019 (11)	0.050 (3)
C28	0.7229 (6)	0.0203 (4)	0.9367 (10)	0.046 (2)
C29	0.6925 (6)	0.0429 (5)	1.0551 (12)	0.074 (3)
C30	0.7152 (7)	0.0204 (5)	1.1785 (12)	0.067 (3)
C31	0.7665 (6)	−0.0273 (4)	1.1870 (11)	0.054 (3)
C32	0.7922 (6)	−0.0521 (4)	1.0698 (11)	0.059 (3)
C33	0.7691 (7)	−0.0298 (5)	0.9440 (11)	0.067 (3)
C34	0.7930 (6)	−0.0448 (4)	1.3288 (11)	0.051 (3)
C35	0.8487 (5)	−0.1332 (4)	1.4497 (10)	0.043 (2)
C36	0.8519 (6)	−0.1071 (4)	1.5777 (11)	0.054 (3)
C37	0.8917 (6)	−0.1383 (5)	1.6737 (11)	0.066 (3)
C38	0.9252 (6)	−0.1944 (4)	1.6521 (10)	0.059 (3)
C39	0.9128 (5)	−0.2159 (4)	1.5248 (10)	0.045 (2)
C40	0.9843 (6)	−0.3092 (5)	1.5509 (13)	0.064 (3)
C41	1.0458 (6)	−0.4098 (5)	1.5385 (14)	0.078 (4)
C42	1.1323 (7)	−0.3867 (5)	1.5446 (14)	0.107 (5)
C43	1.0246 (7)	−0.4309 (5)	1.6746 (14)	0.093 (4)
C44	1.0340 (8)	−0.4579 (5)	1.4328 (19)	0.127 (6)
C45	0.8326 (13)	0.2189 (9)	0.930 (2)	0.213 (9)
C46	0.8531 (11)	0.1593 (9)	1.152 (2)	0.206 (9)
C47	0.5931 (12)	−0.1423 (10)	1.083 (2)	0.23 (1)
C48	0.6808 (13)	−0.2065 (9)	0.9209 (18)	0.221 (10)
H11	0.5906	0.2903	0.7318	0.0677*
H13	0.6799	0.1222	0.8741	0.0626*
H14	0.7988	−0.1290	1.2611	0.0575*
H16	0.9294	−0.2822	1.3904	0.0669*
H18A	0.5166	0.4654	0.7310	0.1549*
H18B	0.4300	0.4873	0.6988	0.1549*
H18C	0.4431	0.4357	0.8007	0.1549*
H19A	0.5360	0.4536	0.4870	0.1356*
H19B	0.4830	0.4094	0.4058	0.1356*
H19C	0.4472	0.4694	0.4538	0.1356*
H20A	0.3384	0.4150	0.5698	0.1074*
H20B	0.3740	0.3532	0.5345	0.1074*
H20C	0.3592	0.3705	0.6845	0.1074*
H23	0.5914	0.2294	0.4009	0.0855*
H24	0.6400	0.1358	0.3506	0.0823*
H25	0.6826	0.0720	0.5276	0.0750*
H29	0.6551	0.0747	1.0517	0.0891*
H30	0.6950	0.0380	1.2592	0.0807*
H32	0.8268	−0.0857	1.0734	0.0702*
H33	0.7854	−0.0494	0.8634	0.0809*
H36	0.8277	−0.0697	1.5962	0.0653*
H37	0.8973	−0.1211	1.7610	0.0795*
H38	0.9538	−0.2157	1.7199	0.0710*
H42A	1.1672	−0.4178	1.5724	0.1281*
H42B	1.1480	−0.3730	1.4576	0.1281*
H42C	1.1354	−0.3549	1.6078	0.1281*
H43A	1.0283	−0.3989	1.7371	0.1116*
H43B	0.9711	−0.4458	1.6740	0.1116*
H43C	1.0606	−0.4615	1.7007	0.1116*
H44A	0.9798	−0.4714	1.4354	0.1524*
H44B	1.0454	−0.4422	1.3456	0.1524*
H44C	1.0693	−0.4900	1.4513	0.1524*
H45A	0.8445	0.1815	0.8903	0.2561*
H45B	0.7985	0.2408	0.8707	0.2561*
H45C	0.8813	0.2403	0.9438	0.2561*
H46A	0.8301	0.1423	1.2314	0.2473*
H46B	0.8650	0.1287	1.0890	0.2473*
H46C	0.9012	0.1797	1.1754	0.2473*
H47A	0.5815	−0.1295	1.1728	0.2781*
H47B	0.6195	−0.1112	1.0354	0.2781*
H47C	0.5444	−0.1522	1.0382	0.2781*
H48A	0.7238	−0.2336	0.9078	0.2648*
H48B	0.6355	−0.2189	0.8693	0.2648*
H48C	0.6970	−0.1680	0.8921	0.2648*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.153 (4)	0.160 (4)	0.151 (4)	−0.013 (3)	−0.041 (4)	−0.042 (3)
S2	0.277 (6)	0.130 (4)	0.134 (4)	−0.073 (4)	−0.085 (5)	0.009 (3)
O3	0.126 (6)	0.113 (6)	0.17 (1)	−0.004 (5)	−0.068 (7)	−0.017 (6)
O4	0.209 (10)	0.108 (6)	0.167 (9)	−0.036 (7)	−0.115 (9)	−0.031 (7)
O5	0.095 (5)	0.060 (5)	0.063 (5)	0.024 (4)	−0.007 (4)	0.006 (4)
O6	0.117 (6)	0.097 (6)	0.040 (4)	0.051 (5)	−0.016 (4)	0.000 (5)
O7	0.119 (6)	0.044 (4)	0.071 (6)	0.020 (4)	−0.010 (5)	0.016 (4)
O8	0.129 (7)	0.043 (4)	0.064 (5)	0.002 (4)	−0.028 (5)	−0.025 (4)
O9	0.086 (5)	0.053 (4)	0.077 (6)	0.022 (4)	−0.021 (4)	−0.001 (4)
O10	0.103 (5)	0.089 (6)	0.086 (6)	0.037 (5)	−0.037 (5)	−0.009 (5)
N11	0.090 (6)	0.035 (4)	0.044 (5)	0.011 (4)	−0.016 (5)	0.002 (4)
N12	0.052 (5)	0.046 (5)	0.039 (5)	0.000 (4)	−0.014 (4)	0.006 (4)
N13	0.074 (6)	0.049 (5)	0.033 (5)	0.017 (4)	−0.020 (4)	−0.012 (4)
N14	0.062 (5)	0.032 (4)	0.050 (5)	0.004 (4)	0.003 (4)	0.007 (4)
N15	0.059 (5)	0.031 (4)	0.046 (5)	0.010 (4)	0.004 (4)	0.006 (4)
N16	0.064 (5)	0.060 (5)	0.043 (5)	0.024 (4)	−0.009 (4)	0.009 (4)
C17	0.086 (8)	0.063 (7)	0.062 (8)	0.025 (6)	0.004 (6)	0.001 (6)
C18	0.18 (1)	0.066 (8)	0.14 (1)	0.055 (9)	−0.01 (1)	−0.040 (9)
C19	0.082 (9)	0.105 (10)	0.15 (1)	0.048 (7)	0.016 (9)	0.06 (1)
C20	0.081 (8)	0.083 (8)	0.104 (10)	0.019 (6)	0.009 (7)	0.013 (8)
C21	0.087 (7)	0.053 (7)	0.029 (6)	0.018 (5)	0.001 (5)	0.012 (5)
C22	0.062 (6)	0.040 (5)	0.046 (6)	0.006 (4)	−0.005 (5)	−0.001 (5)
C23	0.103 (8)	0.068 (7)	0.043 (6)	0.038 (6)	−0.012 (6)	0.001 (5)
C24	0.087 (7)	0.076 (7)	0.043 (6)	0.041 (6)	0.006 (5)	−0.006 (6)
C25	0.086 (7)	0.060 (7)	0.041 (7)	0.018 (5)	−0.007 (6)	−0.004 (6)
C26	0.046 (5)	0.032 (5)	0.055 (7)	0.001 (5)	0.003 (6)	0.006 (5)
C27	0.052 (6)	0.043 (6)	0.055 (7)	0.001 (5)	0.005 (5)	−0.017 (6)
C28	0.069 (6)	0.037 (5)	0.032 (5)	0.011 (5)	−0.001 (5)	0.019 (4)
C29	0.090 (8)	0.068 (7)	0.065 (8)	0.037 (6)	0.010 (7)	0.007 (6)
C30	0.094 (8)	0.058 (7)	0.050 (7)	0.032 (6)	−0.017 (6)	−0.001 (5)
C31	0.062 (6)	0.043 (6)	0.057 (7)	0.003 (5)	−0.001 (6)	−0.007 (5)
C32	0.076 (6)	0.043 (5)	0.056 (7)	0.031 (5)	−0.006 (6)	0.010 (5)
C33	0.094 (8)	0.046 (6)	0.062 (7)	0.018 (6)	0.028 (7)	0.000 (6)
C34	0.052 (6)	0.038 (6)	0.064 (7)	0.000 (5)	−0.016 (6)	0.016 (6)
C35	0.041 (5)	0.042 (6)	0.048 (7)	0.006 (5)	−0.011 (5)	0.001 (5)
C36	0.062 (6)	0.047 (6)	0.055 (7)	0.015 (5)	−0.008 (5)	−0.009 (6)
C37	0.084 (7)	0.073 (7)	0.041 (6)	0.016 (6)	−0.008 (6)	−0.012 (5)
C38	0.070 (6)	0.064 (6)	0.043 (6)	0.015 (5)	−0.019 (5)	−0.006 (5)
C39	0.049 (5)	0.044 (5)	0.041 (6)	0.009 (4)	−0.008 (5)	0.005 (5)
C40	0.045 (6)	0.073 (8)	0.073 (9)	0.003 (5)	0.000 (6)	−0.009 (7)
C41	0.067 (7)	0.065 (8)	0.10 (1)	0.025 (6)	0.014 (7)	0.028 (8)
C42	0.070 (8)	0.111 (9)	0.14 (1)	0.035 (7)	0.001 (9)	0.052 (10)
C43	0.101 (9)	0.102 (9)	0.077 (8)	0.021 (7)	0.001 (8)	0.036 (8)
C44	0.13 (1)	0.075 (9)	0.18 (2)	0.035 (8)	0.02 (1)	−0.01 (1)
C45	0.22 (2)	0.24 (2)	0.17 (2)	−0.05 (2)	0.07 (2)	−0.06 (2)
C46	0.15 (2)	0.25 (2)	0.22 (2)	−0.03 (1)	−0.01 (2)	0.07 (2)
C47	0.17 (2)	0.27 (2)	0.26 (3)	−0.03 (2)	−0.04 (2)	0.05 (2)
C48	0.24 (2)	0.31 (3)	0.11 (1)	0.02 (2)	−0.07 (1)	−0.10 (2)

Geometric parameters (Å, º) top

S1—O3	1.46 (1)	C24—H24	0.950
S1—C45	1.70 (2)	C25—C26	1.37 (1)
S1—C46	1.73 (2)	C25—H25	0.950
S2—O4	1.45 (1)	C27—C28	1.48 (1)
S2—C47	1.74 (2)	C28—C29	1.37 (1)
S2—C48	1.71 (2)	C28—C33	1.37 (1)
O5—C17	1.49 (1)	C29—C30	1.37 (2)
O5—C21	1.38 (1)	C29—H29	0.950
O6—C21	1.14 (1)	C30—C31	1.37 (1)
O7—C27	1.24 (1)	C30—H30	0.950
O8—C34	1.15 (1)	C31—C32	1.35 (2)
O9—C40	1.34 (1)	C31—C34	1.52 (2)
O9—C41	1.48 (1)	C32—C33	1.39 (2)
O10—C40	1.25 (1)	C32—H32	0.950
N11—C21	1.38 (1)	C33—H33	0.950
N11—C22	1.40 (1)	C35—C36	1.39 (1)
N11—H11	0.950	C36—C37	1.35 (1)
N12—C22	1.31 (1)	C36—H36	0.950
N12—C26	1.37 (1)	C37—C38	1.40 (1)
N13—C26	1.41 (1)	C37—H37	0.950
N13—C27	1.32 (1)	C38—C39	1.36 (1)
N13—H13	0.950	C38—H38	0.950
N14—C34	1.39 (1)	C41—C42	1.53 (1)
N14—C35	1.42 (1)	C41—C43	1.47 (2)
N14—H14	0.950	C41—C44	1.52 (2)
N15—C35	1.31 (1)	C42—H42A	0.950
N15—C39	1.35 (1)	C42—H42B	0.949
N16—C39	1.40 (1)	C42—H42C	0.951
N16—C40	1.30 (1)	C43—H43A	0.951
N16—H16	0.950	C43—H43B	0.950
C17—C18	1.50 (2)	C43—H43C	0.949
C17—C19	1.50 (2)	C44—H44A	0.950
C17—C20	1.47 (2)	C44—H44B	0.950
C18—H18A	0.950	C44—H44C	0.949
C18—H18B	0.950	C45—H45A	0.950
C18—H18C	0.950	C45—H45B	0.951
C19—H19A	0.950	C45—H45C	0.949
C19—H19B	0.950	C46—H46A	0.950
C19—H19C	0.951	C46—H46B	0.950
C20—H20A	0.950	C46—H46C	0.950
C20—H20B	0.950	C47—H47A	0.950
C20—H20C	0.951	C47—H47B	0.950
C22—C23	1.38 (1)	C47—H47C	0.950
C23—C24	1.36 (1)	C48—H48A	0.949
C23—H23	0.950	C48—H48B	0.950
C24—C25	1.40 (1)	C48—H48C	0.951

O3—S1—C45	103.0 (9)	C30—C31—C34	116.1 (9)
O3—S1—C46	108.4 (8)	C32—C31—C34	126.1 (9)
C45—S1—C46	98 (1)	C31—C32—C33	121.7 (9)
O4—S2—C47	104.2 (8)	C31—C32—H32	119.2
O4—S2—C48	105.5 (9)	C33—C32—H32	119.2
C47—S2—C48	97 (1)	C28—C33—C32	120.0 (10)
C17—O5—C21	119.5 (8)	C28—C33—H33	120.0
C40—O9—C41	123.6 (9)	C32—C33—H33	120.0
C21—N11—C22	125.4 (8)	O8—C34—N14	127.8 (10)
C21—N11—H11	117.3	O8—C34—C31	120.3 (9)
C22—N11—H11	117.3	N14—C34—C31	111.8 (8)
C22—N12—C26	117.7 (8)	N14—C35—N15	113.7 (8)
C26—N13—C27	128.2 (8)	N14—C35—C36	122.4 (8)
C26—N13—H13	115.9	N15—C35—C36	123.9 (8)
C27—N13—H13	115.9	C35—C36—C37	115.7 (9)
C34—N14—C35	125.4 (8)	C35—C36—H36	122.2
C34—N14—H14	117.3	C37—C36—H36	122.1
C35—N14—H14	117.3	C36—C37—C38	123.9 (10)
C35—N15—C39	116.9 (8)	C36—C37—H37	118.0
C39—N16—C40	127.1 (9)	C38—C37—H37	118.0
C39—N16—H16	116.4	C37—C38—C39	113.7 (9)
C40—N16—H16	116.5	C37—C38—H38	123.1
O5—C17—C18	102.2 (9)	C39—C38—H38	123.1
O5—C17—C19	109.9 (9)	N15—C39—N16	111.0 (8)
O5—C17—C20	111.3 (8)	N15—C39—C38	125.6 (8)
C18—C17—C19	109.8 (10)	N16—C39—C38	123.2 (8)
C18—C17—C20	110 (1)	O9—C40—O10	121.6 (10)
C19—C17—C20	112 (1)	O9—C40—N16	113 (1)
C17—C18—H18A	109.5	O10—C40—N16	125 (1)
C17—C18—H18B	109.5	O9—C41—C42	109.9 (8)
C17—C18—H18C	109.5	O9—C41—C43	112.4 (9)
H18A—C18—H18B	109.5	O9—C41—C44	102.5 (10)
H18A—C18—H18C	109.4	C42—C41—C43	107 (1)
H18B—C18—H18C	109.4	C42—C41—C44	113 (1)
C17—C19—H19A	109.5	C43—C41—C44	111 (1)
C17—C19—H19B	109.5	C41—C42—H42A	109.4
C17—C19—H19C	109.5	C41—C42—H42B	109.5
H19A—C19—H19B	109.5	C41—C42—H42C	109.4
H19A—C19—H19C	109.4	H42A—C42—H42B	109.5
H19B—C19—H19C	109.5	H42A—C42—H42C	109.4
C17—C20—H20A	109.5	H42B—C42—H42C	109.5
C17—C20—H20B	109.5	C41—C43—H43A	109.4
C17—C20—H20C	109.4	C41—C43—H43B	109.4
H20A—C20—H20B	109.5	C41—C43—H43C	109.5
H20A—C20—H20C	109.5	H43A—C43—H43B	109.4
H20B—C20—H20C	109.4	H43A—C43—H43C	109.5
O5—C21—O6	125.9 (10)	H43B—C43—H43C	109.6
O5—C21—N11	104.8 (8)	C41—C44—H44A	109.4
O6—C21—N11	129.3 (10)	C41—C44—H44B	109.4
N11—C22—N12	113.8 (8)	C41—C44—H44C	109.4
N11—C22—C23	123.0 (9)	H44A—C44—H44B	109.5
N12—C22—C23	123.0 (8)	H44A—C44—H44C	109.5
C22—C23—C24	118.9 (9)	H44B—C44—H44C	109.6
C22—C23—H23	120.6	S1—C45—H45A	109.5
C24—C23—H23	120.6	S1—C45—H45B	109.5
C23—C24—C25	120.5 (9)	S1—C45—H45C	109.5
C23—C24—H24	119.8	H45A—C45—H45B	109.4
C25—C24—H24	119.7	H45A—C45—H45C	109.5
C24—C25—C26	116.6 (9)	H45B—C45—H45C	109.5
C24—C25—H25	121.7	S1—C46—H46A	109.5
C26—C25—H25	121.7	S1—C46—H46B	109.5
N12—C26—N13	112.2 (8)	S1—C46—H46C	109.5
N12—C26—C25	123.3 (9)	H46A—C46—H46B	109.5
N13—C26—C25	124.5 (8)	H46A—C46—H46C	109.5
O7—C27—N13	121.0 (9)	H46B—C46—H46C	109.5
O7—C27—C28	120.4 (9)	S2—C47—H47A	109.5
N13—C27—C28	118.5 (9)	S2—C47—H47B	109.4
C27—C28—C29	123.1 (9)	S2—C47—H47C	109.5
C27—C28—C33	118.8 (9)	H47A—C47—H47B	109.4
C29—C28—C33	117.9 (9)	H47A—C47—H47C	109.5
C28—C29—C30	121.3 (10)	H47B—C47—H47C	109.5
C28—C29—H29	119.4	S2—C48—H48A	109.5
C30—C29—H29	119.3	S2—C48—H48B	109.5
C29—C30—C31	120 (1)	S2—C48—H48C	109.4
C29—C30—H30	119.6	H48A—C48—H48B	109.5
C31—C30—H30	119.5	H48A—C48—H48C	109.4
C30—C31—C32	117 (1)	H48B—C48—H48C	109.4

O5—C21—N11—C22	−179.3 (8)	N16—C40—O9—C41	170.7 (9)
O6—C21—O5—C17	9 (1)	C18—C17—O5—C21	177.7 (9)
O6—C21—N11—C22	0 (1)	C19—C17—O5—C21	−65 (1)
O7—C27—N13—C26	3 (1)	C20—C17—O5—C21	60 (1)
O7—C27—C28—C29	−154.9 (10)	C21—N11—C22—C23	23 (1)
O7—C27—C28—C33	18 (1)	C22—N12—C26—C25	0 (1)
O8—C34—N14—C35	−5 (1)	C22—C23—C24—C25	−1 (1)
O8—C34—C31—C30	−30 (1)	C23—C22—N12—C26	−1 (1)
O8—C34—C31—C32	145 (1)	C23—C24—C25—C26	0 (1)
O9—C40—N16—C39	169.0 (8)	C25—C26—N13—C27	−10 (1)
O10—C40—O9—C41	−7 (1)	C26—N13—C27—C28	−179.1 (8)
O10—C40—N16—C39	−12 (1)	C27—C28—C29—C30	−179.0 (10)
N11—C21—O5—C17	−170.6 (8)	C27—C28—C33—C32	178.4 (9)
N11—C22—N12—C26	−178.0 (7)	C28—C29—C30—C31	−2 (1)
N11—C22—C23—C24	178.1 (9)	C28—C33—C32—C31	3 (1)
N12—C22—N11—C21	−160.9 (9)	C29—C28—C33—C32	−7 (1)
N12—C22—C23—C24	2 (1)	C29—C30—C31—C32	−1 (1)
N12—C26—N13—C27	170.8 (8)	C29—C30—C31—C34	174.8 (9)
N12—C26—C25—C24	0 (1)	C30—C29—C28—C33	7 (1)
N13—C26—N12—C22	179.6 (7)	C30—C31—C32—C33	1 (1)
N13—C26—C25—C24	−178.6 (9)	C31—C34—N14—C35	170.9 (8)
N13—C27—C28—C29	27 (1)	C33—C32—C31—C34	−174.9 (10)
N13—C27—C28—C33	−159.2 (9)	C34—N14—C35—C36	16 (1)
N14—C34—C31—C30	152.4 (9)	C35—N15—C39—C38	−4 (1)
N14—C34—C31—C32	−31 (1)	C35—C36—C37—C38	−2 (1)
N14—C35—N15—C39	−179.2 (7)	C36—C35—N15—C39	0 (1)
N14—C35—C36—C37	−177.5 (8)	C36—C37—C38—C39	−1 (1)
N15—C35—N14—C34	−164.4 (8)	C38—C39—N16—C40	0 (1)
N15—C35—C36—C37	3 (1)	C40—O9—C41—C42	−56 (1)
N15—C39—N16—C40	174.2 (9)	C40—O9—C41—C43	62 (1)
N15—C39—C38—C37	5 (1)	C40—O9—C41—C44	−177.2 (10)
N16—C39—N15—C35	−179.3 (7)	C40—O9—C41—C44	−177.2 (10)
N16—C39—C38—C37	179.4 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···N15ⁱ	0.95	2.02	2.968 (11)	176
N13—H13···O3	0.95	2.13	3.055 (12)	165
N14—H14···O4	0.95	1.98	2.864 (13)	153
N16—H16···N12ⁱⁱ	0.95	2.15	3.083 (11)	167

Symmetry codes: (i) −x+3/2, y+1/2, z−1/2; (ii) −x+3/2, y−1/2, z+1/2.

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page