(S)-(–)-1-Phenyl­ethyl­aminium 3,5-di­nitro­salicyl­ate

Smith, G.; Wermuth, U.D.; White, J.M.

doi:10.1107/S1600536803024668

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(S)-(–)-1-Phenylethylaminium 3,5-dinitrosalicylate

G. Smith, U. D. Wermuth and J. M. White

The crystal structure of the 1:1 proton-transfer compound of 3,5-dinitrosalicylic acid with the optically active amine (S)-(−)-1-phenylethylamine, viz. (S)-(−)-1-phenylethylaminium 3,5-dinitrosalicylate, C₈H₁₂N⁺·C₇H₃N₂O₇⁻, shows the presence of two pseudo-centrosymmetrically related and conformationally similar carboxylate anions and two chiral but conformationally different (S)-aminium cations in the crystallographic repeat unit. In these cations, the protonated amine-N atoms have a number of hydrogen-bonding associations with carboxyl, phenol and nitro O atoms of the acid [N

O = 2.824 (4)–3.245 (5) Å]. These, together with peripheral hydrogen-bonding associations and some weak cation–anion π–π interactions, result in a three-dimensional network polymer structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024668/ww6138sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024668/ww6138Isup2.hkl Contains datablock I

CCDC reference: 227902

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R factor = 0.045
wR factor = 0.107
Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry .....         96 PerFit
PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup .        P-1

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.20
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ....... =          2
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....       C41C
PLAT243_ALERT_4_C High Solvent U(eq) as Compared to Neighbors ....       C51C
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....       C11C
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.37
PLAT331_ALERT_2_C Small Av. Phenyl C-C Dist. C11C   -   C61C     =       1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               3494
           Count of symmetry unique reflns         3641
           Completeness (_total/calc)             95.96%
           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
   2 ALERT level B = Potentially serious problem
  10 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

(S)-(-)-1-phenylethylaminium 3,5-dinitrosalicylate top

Crystal data top

C₈H₁₂N⁺·C₇H₃N₂O₇⁻	Z = 2
M_r = 349.30	F(000) = 364
Triclinic, P1	D_x = 1.464 Mg m⁻³
Hall symbol: P 1	Melting point = 477–480 K
a = 7.5177 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6277 (10) Å	Cell parameters from 1643 reflections
c = 11.1566 (12) Å	θ = 2.8–26.0°
α = 89.008 (2)°	µ = 0.12 mm⁻¹
β = 79.373 (2)°	T = 293 K
γ = 87.054 (2)°	Block, yellow
V = 792.57 (15) Å³	0.25 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD-detector diffractometer	2511 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
φ and ω scans	h = −7→9
5055 measured reflections	k = −12→12
3494 independent reflections	l = −14→14

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 0.93	w = 1/[σ²(F_o²) + (0.0612P)²] where P = (F_o² + 2F_c²)/3
3494 reflections	(Δ/σ)_max = 0.013
485 parameters	Δρ_max = 0.20 e Å⁻³
3 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 (Å²) top

	x	y	z	U_iso*/U_eq
N71C	−0.1421 (4)	0.5008 (3)	0.8795 (3)	0.0479 (11)
C11C	0.0552 (5)	0.2846 (4)	0.8639 (4)	0.0521 (14)
C21C	0.0713 (7)	0.2207 (6)	0.9719 (5)	0.0804 (19)
C31C	0.0727 (9)	0.0760 (8)	0.9820 (8)	0.123 (3)
C41C	0.0610 (9)	0.0021 (7)	0.8822 (12)	0.139 (5)
C51C	0.0440 (8)	0.0631 (7)	0.7763 (9)	0.123 (3)*
C61C	0.0412 (6)	0.2059 (5)	0.7661 (5)	0.0737 (17)
C71C	0.0500 (5)	0.4421 (4)	0.8490 (4)	0.0597 (12)
C81C	0.1640 (7)	0.5175 (6)	0.9235 (7)	0.109 (3)
N71D	0.5405 (4)	0.3707 (4)	0.3167 (3)	0.0470 (11)
C11B	0.3562 (5)	0.5906 (4)	0.3184 (4)	0.0470 (9)*
C21D	0.3426 (6)	0.6272 (5)	0.4386 (4)	0.0591 (14)
C31D	0.3221 (6)	0.7656 (5)	0.4730 (5)	0.0727 (17)
C41D	0.3146 (6)	0.8688 (5)	0.3874 (6)	0.083 (2)
C51D	0.3239 (7)	0.8337 (5)	0.2685 (6)	0.0816 (19)
C61D	0.3460 (6)	0.6963 (5)	0.2339 (4)	0.0649 (16)
C71D	0.3801 (5)	0.4427 (4)	0.2755 (4)	0.0557 (12)
C81D	0.2167 (6)	0.3577 (5)	0.3195 (5)	0.088 (2)
O2A	0.5815 (4)	0.3411 (3)	0.8171 (2)	0.0551 (10)
O31A	0.6446 (5)	0.3017 (3)	1.0417 (3)	0.0709 (11)
O32A	0.5507 (5)	0.1174 (3)	1.1338 (3)	0.0795 (13)
O51A	0.5316 (4)	−0.2965 (3)	0.9149 (3)	0.0691 (11)
O52A	0.4768 (5)	−0.2837 (3)	0.7315 (3)	0.0790 (13)
O71A	0.4661 (4)	0.1627 (3)	0.5153 (3)	0.0721 (11)
O72A	0.5077 (5)	0.3531 (3)	0.6106 (3)	0.0701 (11)
N3A	0.5931 (4)	0.1853 (3)	1.0404 (3)	0.0496 (11)
N5A	0.5110 (5)	−0.2309 (3)	0.8228 (4)	0.0562 (12)
C1A	0.5258 (5)	0.1374 (4)	0.7175 (3)	0.0441 (11)
C2A	0.5645 (5)	0.2102 (4)	0.8214 (3)	0.0423 (12)
C3A	0.5737 (5)	0.1239 (4)	0.9257 (3)	0.0419 (12)
C4A	0.5591 (5)	−0.0184 (4)	0.9260 (3)	0.0432 (12)
C5A	0.5298 (5)	−0.0804 (4)	0.8220 (3)	0.0449 (12)
C6A	0.5105 (5)	−0.0026 (4)	0.7185 (3)	0.0461 (12)
C7A	0.4983 (5)	0.2179 (5)	0.6062 (4)	0.0551 (14)
O2B	0.8051 (4)	0.5320 (3)	0.3892 (2)	0.0541 (10)
O31B	0.7784 (4)	0.5660 (3)	0.1558 (2)	0.0695 (11)
O32B	0.8337 (6)	0.7631 (4)	0.0725 (3)	0.0879 (13)
O51B	0.8568 (4)	1.1709 (3)	0.2954 (3)	0.0730 (11)
O52B	0.8925 (4)	1.1575 (3)	0.4824 (3)	0.0738 (11)
O71B	0.8948 (4)	0.7153 (3)	0.6966 (2)	0.0645 (10)
O72B	0.8597 (5)	0.5219 (3)	0.6020 (3)	0.0689 (13)
N3B	0.8096 (4)	0.6892 (4)	0.1641 (3)	0.0528 (12)
N5B	0.8670 (4)	1.1038 (3)	0.3890 (3)	0.0540 (12)
C1B	0.8472 (5)	0.7356 (4)	0.4925 (4)	0.0451 (12)
C2B	0.8209 (5)	0.6635 (4)	0.3864 (3)	0.0424 (12)
C3B	0.8156 (5)	0.7498 (4)	0.2806 (3)	0.0444 (12)
C4B	0.8269 (5)	0.8917 (4)	0.2830 (4)	0.0467 (12)
C5B	0.8472 (5)	0.9552 (4)	0.3880 (4)	0.0458 (12)
C6B	0.8584 (5)	0.8778 (4)	0.4924 (3)	0.0456 (12)
C7B	0.8690 (5)	0.6583 (4)	0.6055 (4)	0.0492 (12)
H21C	0.081500	0.273900	1.038900	0.0960*
H31C	0.081400	0.031700	1.055500	0.1480*
H41C	0.064900	−0.094500	0.887500	0.1670*
H51C	0.034000	0.009400	0.709600	0.1480*
H61C	0.029800	0.248600	0.692400	0.0890*
H71C	0.095500	0.463000	0.762900	0.0720*
H72C	−0.200 (7)	0.426 (6)	0.852 (5)	0.085 (10)*
H73C	−0.142 (4)	0.577 (4)	0.839 (3)	0.056 (8)*
H74C	−0.163 (6)	0.519 (5)	0.963 (4)	0.076 (13)*
H81C	0.288400	0.485000	0.901200	0.130*
H82C	0.122000	0.499400	1.008700	0.130*
H83C	0.153700	0.615600	0.907900	0.130*
H21D	0.347200	0.558200	0.497500	0.0710*
H31D	0.313500	0.788600	0.554500	0.0870*
H41D	0.303200	0.961700	0.410300	0.1000*
H51D	0.315300	0.902900	0.210300	0.0980*
H61D	0.354300	0.674200	0.152200	0.0780*
H71D	0.403100	0.443600	0.186100	0.0670*
H72D	0.526 (9)	0.328 (6)	0.395 (6)	0.075 (15)*
H73D	0.624 (5)	0.434 (4)	0.326 (3)	0.063 (9)*
H74D	0.581 (5)	0.309 (4)	0.271 (3)	0.065 (11)*
H81D	0.194700	0.352400	0.407000	0.105*
H82D	0.238900	0.265700	0.286600	0.105*
H83D	0.112700	0.401100	0.293000	0.105*
H4A	0.568900	−0.071200	0.995200	0.0520*
H6A	0.487200	−0.046500	0.649900	0.0550*
H72A	0.552 (7)	0.383 (6)	0.679 (5)	0.111 (18)*
H4B	0.820700	0.944600	0.213200	0.0560*
H6B	0.873700	0.922200	0.562900	0.0540*
H72B	0.837 (6)	0.503 (4)	0.536 (4)	0.056 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N71C	0.058 (2)	0.0372 (17)	0.047 (2)	0.0013 (14)	−0.0072 (15)	0.0069 (15)
C11C	0.044 (2)	0.048 (2)	0.062 (3)	−0.0007 (16)	−0.0041 (17)	0.0015 (18)
C21C	0.071 (3)	0.094 (4)	0.071 (3)	0.006 (2)	−0.004 (2)	0.019 (3)
C31C	0.082 (4)	0.108 (5)	0.157 (7)	0.023 (4)	0.021 (4)	0.074 (5)
C41C	0.056 (3)	0.061 (4)	0.278 (13)	0.007 (3)	0.024 (6)	0.033 (6)
C61C	0.062 (3)	0.074 (3)	0.089 (3)	0.009 (2)	−0.025 (2)	−0.028 (3)
C71C	0.054 (2)	0.052 (2)	0.065 (2)	0.0006 (16)	0.0085 (17)	0.0065 (18)
C81C	0.052 (3)	0.078 (4)	0.199 (7)	−0.007 (2)	−0.027 (3)	−0.037 (4)
N71D	0.0504 (19)	0.0413 (18)	0.050 (2)	0.0002 (15)	−0.0111 (15)	−0.0036 (16)
C21D	0.066 (3)	0.053 (2)	0.060 (2)	0.0066 (18)	−0.0186 (19)	0.0018 (18)
C31D	0.064 (3)	0.082 (3)	0.077 (3)	0.008 (2)	−0.027 (2)	−0.026 (2)
C41D	0.060 (3)	0.054 (3)	0.138 (5)	0.003 (2)	−0.027 (3)	−0.016 (3)
C51D	0.069 (3)	0.064 (3)	0.106 (4)	0.003 (2)	−0.005 (3)	0.029 (3)
C61D	0.061 (3)	0.069 (3)	0.063 (2)	0.005 (2)	−0.0106 (19)	0.016 (2)
C71D	0.057 (2)	0.054 (2)	0.057 (2)	0.0051 (16)	−0.0149 (17)	−0.0050 (17)
C81D	0.058 (3)	0.058 (3)	0.148 (5)	−0.007 (2)	−0.019 (3)	−0.014 (3)
O2A	0.0691 (19)	0.0425 (17)	0.0580 (17)	−0.0072 (13)	−0.0220 (14)	0.0057 (13)
O31A	0.105 (2)	0.0543 (19)	0.0527 (17)	−0.0230 (16)	−0.0065 (15)	−0.0071 (14)
O32A	0.129 (3)	0.066 (2)	0.0448 (17)	−0.0194 (19)	−0.0159 (17)	0.0073 (15)
O51A	0.094 (2)	0.0444 (17)	0.071 (2)	−0.0050 (15)	−0.0212 (17)	0.0133 (16)
O52A	0.116 (3)	0.0523 (18)	0.076 (2)	−0.0194 (17)	−0.0320 (19)	−0.0044 (17)
O71A	0.095 (2)	0.075 (2)	0.0511 (18)	−0.0185 (17)	−0.0230 (16)	0.0128 (16)
O72A	0.097 (2)	0.0526 (19)	0.067 (2)	−0.0102 (16)	−0.0320 (17)	0.0234 (16)
N3A	0.059 (2)	0.049 (2)	0.0408 (19)	−0.0002 (15)	−0.0098 (14)	0.0009 (15)
N5A	0.063 (2)	0.041 (2)	0.065 (2)	−0.0076 (15)	−0.0120 (18)	0.0023 (19)
C1A	0.043 (2)	0.049 (2)	0.0396 (19)	−0.0015 (16)	−0.0066 (15)	0.0099 (16)
C2A	0.038 (2)	0.039 (2)	0.050 (2)	0.0004 (16)	−0.0091 (16)	0.0034 (18)
C3A	0.043 (2)	0.042 (2)	0.040 (2)	0.0045 (16)	−0.0080 (16)	0.0023 (17)
C4A	0.044 (2)	0.038 (2)	0.045 (2)	0.0010 (15)	−0.0034 (16)	0.0091 (17)
C5A	0.046 (2)	0.037 (2)	0.050 (2)	−0.0001 (15)	−0.0050 (16)	0.0008 (17)
C6A	0.048 (2)	0.043 (2)	0.047 (2)	−0.0062 (15)	−0.0069 (17)	0.0004 (17)
C7A	0.056 (2)	0.059 (3)	0.050 (2)	−0.0065 (19)	−0.0092 (18)	0.012 (2)
O2B	0.0685 (18)	0.0335 (15)	0.0611 (18)	−0.0002 (12)	−0.0155 (14)	0.0057 (13)
O31B	0.104 (2)	0.0518 (19)	0.0519 (17)	−0.0201 (15)	−0.0069 (15)	−0.0066 (13)
O32B	0.156 (3)	0.064 (2)	0.0485 (18)	−0.021 (2)	−0.0284 (19)	0.0110 (16)
O51B	0.093 (2)	0.0426 (17)	0.087 (2)	−0.0023 (15)	−0.0277 (18)	0.0159 (16)
O52B	0.096 (2)	0.0507 (18)	0.077 (2)	−0.0113 (15)	−0.0190 (18)	−0.0083 (17)
O71B	0.087 (2)	0.0621 (17)	0.0471 (16)	−0.0126 (15)	−0.0174 (14)	0.0066 (14)
O72B	0.108 (3)	0.0495 (19)	0.0544 (19)	−0.0149 (15)	−0.0262 (17)	0.0093 (15)
N3B	0.056 (2)	0.051 (2)	0.050 (2)	−0.0064 (15)	−0.0055 (15)	0.0024 (17)
N5B	0.058 (2)	0.042 (2)	0.062 (2)	0.0002 (15)	−0.0117 (17)	0.0021 (18)
C1B	0.042 (2)	0.044 (2)	0.048 (2)	−0.0047 (16)	−0.0040 (16)	0.0001 (17)
C2B	0.040 (2)	0.041 (2)	0.044 (2)	0.0023 (16)	−0.0034 (15)	0.0042 (17)
C3B	0.045 (2)	0.044 (2)	0.043 (2)	−0.0027 (16)	−0.0051 (16)	−0.0014 (18)
C4B	0.044 (2)	0.048 (2)	0.049 (2)	−0.0023 (16)	−0.0117 (17)	0.0086 (18)
C5B	0.041 (2)	0.040 (2)	0.055 (2)	0.0002 (15)	−0.0056 (16)	0.0017 (18)
C6B	0.050 (2)	0.046 (2)	0.040 (2)	−0.0035 (16)	−0.0060 (16)	−0.0029 (17)
C7B	0.059 (2)	0.046 (2)	0.044 (2)	−0.0092 (17)	−0.0116 (17)	0.0062 (17)

Geometric parameters (Å, º) top

O2A—C2A	1.272 (5)	C61C—H61C	0.9290
O31A—N3A	1.205 (4)	C71C—H71C	0.9795
O32A—N3A	1.221 (5)	C81C—H83C	0.9592
O51A—N5A	1.227 (5)	C81C—H82C	0.9606
O52A—N5A	1.221 (5)	C81C—H81C	0.9598
O71A—C7A	1.221 (5)	C11B—C71D	1.502 (6)
O72A—C7A	1.309 (6)	C11B—C21D	1.377 (6)
O72A—H72A	0.94 (5)	C11B—C61D	1.384 (6)
O2B—C2B	1.277 (5)	C21D—C31D	1.386 (7)
O31B—N3B	1.229 (5)	C31D—C41D	1.372 (8)
O32B—N3B	1.226 (5)	C41D—C51D	1.363 (9)
O51B—N5B	1.231 (5)	C51D—C61D	1.378 (7)
O52B—N5B	1.222 (5)	C71D—C81D	1.512 (6)
O71B—C7B	1.214 (5)	C21D—H21D	0.9302
O72B—C7B	1.320 (5)	C31D—H31D	0.9294
O72B—H72B	0.81 (4)	C41D—H41D	0.9298
N71C—C71C	1.504 (5)	C51D—H51D	0.9304
N71C—H74C	0.93 (4)	C61D—H61D	0.9297
N71C—H73C	0.85 (4)	C71D—H71D	0.9803
N71C—H72C	0.94 (6)	C81D—H83D	0.9595
N71D—C71D	1.501 (5)	C81D—H82D	0.9595
N71D—H73D	0.92 (4)	C81D—H81D	0.9605
N71D—H74D	0.80 (4)	C1A—C2A	1.447 (5)
N71D—H72D	0.95 (6)	C1A—C6A	1.358 (5)
N3A—C3A	1.453 (5)	C1A—C7A	1.493 (6)
N5A—C5A	1.463 (5)	C2A—C3A	1.428 (5)
N3B—C3B	1.443 (5)	C3A—C4A	1.380 (5)
N5B—C5B	1.446 (5)	C4A—C5A	1.372 (5)
C11C—C71C	1.522 (5)	C5A—C6A	1.391 (5)
C11C—C61C	1.362 (7)	C4A—H4A	0.9292
C11C—C21C	1.366 (7)	C6A—H6A	0.9292
C21C—C31C	1.395 (10)	C1B—C6B	1.376 (5)
C31C—C41C	1.350 (14)	C1B—C7B	1.484 (6)
C41C—C51C	1.335 (15)	C1B—C2B	1.432 (5)
C51C—C61C	1.377 (8)	C2B—C3B	1.437 (5)
C71C—C81C	1.517 (7)	C3B—C4B	1.374 (5)
C21C—H21C	0.9303	C4B—C5B	1.367 (6)
C31C—H31C	0.9292	C5B—C6B	1.385 (5)
C41C—H41C	0.9302	C4B—H4B	0.9302
C51C—H51C	0.9299	C6B—H6B	0.9299

C7A—O72A—H72A	113 (4)	C11B—C71D—C81D	113.7 (4)
C7B—O72B—H72B	107 (3)	N71D—C71D—C81D	108.0 (3)
H73C—N71C—H74C	110 (4)	N71D—C71D—C11B	110.6 (3)
C71C—N71C—H74C	106 (3)	C11B—C21D—H21D	119.60
C71C—N71C—H72C	98 (3)	C31D—C21D—H21D	119.56
C71C—N71C—H73C	105 (2)	C41D—C31D—H31D	119.84
H72C—N71C—H74C	118 (4)	C21D—C31D—H31D	119.78
H72C—N71C—H73C	117 (4)	C31D—C41D—H41D	120.34
C71D—N71D—H74D	110 (3)	C51D—C41D—H41D	120.34
C71D—N71D—H73D	110 (2)	C41D—C51D—H51D	119.85
C71D—N71D—H72D	120 (4)	C61D—C51D—H51D	119.76
H72D—N71D—H73D	99 (4)	C51D—C61D—H61D	119.34
H72D—N71D—H74D	104 (4)	C11B—C61D—H61D	119.39
H73D—N71D—H74D	114 (4)	C11B—C71D—H71D	108.20
O32A—N3A—C3A	118.1 (3)	C81D—C71D—H71D	108.12
O31A—N3A—O32A	121.9 (3)	N71D—C71D—H71D	108.08
O31A—N3A—C3A	119.9 (3)	H81D—C81D—H83D	109.43
O51A—N5A—C5A	118.0 (3)	C71D—C81D—H82D	109.51
O52A—N5A—C5A	118.0 (3)	C71D—C81D—H83D	109.48
O51A—N5A—O52A	124.0 (3)	C71D—C81D—H81D	109.46
O32B—N3B—C3B	119.0 (4)	H82D—C81D—H83D	109.49
O31B—N3B—C3B	121.1 (3)	H81D—C81D—H82D	109.46
O31B—N3B—O32B	119.9 (3)	C2A—C1A—C7A	119.5 (3)
O52B—N5B—C5B	118.9 (3)	C6A—C1A—C7A	118.6 (3)
O51B—N5B—O52B	122.8 (3)	C2A—C1A—C6A	122.0 (3)
O51B—N5B—C5B	118.4 (3)	C1A—C2A—C3A	114.3 (3)
C21C—C11C—C71C	122.2 (4)	O2A—C2A—C3A	125.0 (3)
C21C—C11C—C61C	119.5 (4)	O2A—C2A—C1A	120.6 (3)
C61C—C11C—C71C	118.4 (4)	N3A—C3A—C2A	120.2 (3)
C11C—C21C—C31C	120.2 (6)	C2A—C3A—C4A	123.3 (3)
C21C—C31C—C41C	118.3 (8)	N3A—C3A—C4A	116.4 (3)
C31C—C41C—C51C	122.2 (7)	C3A—C4A—C5A	118.6 (3)
C41C—C51C—C61C	119.8 (8)	C4A—C5A—C6A	121.4 (4)
C11C—C61C—C51C	120.1 (6)	N5A—C5A—C6A	119.8 (3)
N71C—C71C—C11C	110.3 (3)	N5A—C5A—C4A	118.7 (3)
N71C—C71C—C81C	108.6 (4)	C1A—C6A—C5A	120.1 (3)
C11C—C71C—C81C	115.2 (4)	O71A—C7A—C1A	122.7 (4)
C31C—C21C—H21C	119.93	O72A—C7A—C1A	116.6 (4)
C11C—C21C—H21C	119.83	O71A—C7A—O72A	120.7 (4)
C21C—C31C—H31C	120.84	C3A—C4A—H4A	120.70
C41C—C31C—H31C	120.90	C5A—C4A—H4A	120.65
C31C—C41C—H41C	118.88	C5A—C6A—H6A	119.94
C51C—C41C—H41C	118.95	C1A—C6A—H6A	119.92
C61C—C51C—H51C	120.07	C2B—C1B—C6B	121.5 (4)
C41C—C51C—H51C	120.15	C2B—C1B—C7B	120.8 (3)
C51C—C61C—H61C	119.95	C6B—C1B—C7B	117.7 (4)
C11C—C61C—H61C	119.97	O2B—C2B—C3B	124.3 (3)
C81C—C71C—H71C	107.48	C1B—C2B—C3B	115.0 (3)
C11C—C71C—H71C	107.50	O2B—C2B—C1B	120.7 (3)
N71C—C71C—H71C	107.50	N3B—C3B—C2B	120.8 (3)
C71C—C81C—H82C	109.44	C2B—C3B—C4B	122.3 (3)
H81C—C81C—H82C	109.42	N3B—C3B—C4B	116.8 (3)
H81C—C81C—H83C	109.52	C3B—C4B—C5B	120.0 (4)
C71C—C81C—H81C	109.47	N5B—C5B—C6B	119.3 (4)
H82C—C81C—H83C	109.50	C4B—C5B—C6B	120.7 (4)
C71C—C81C—H83C	109.49	N5B—C5B—C4B	120.0 (4)
C21D—C11B—C71D	123.3 (4)	C1B—C6B—C5B	120.5 (4)
C61D—C11B—C71D	119.0 (4)	O71B—C7B—C1B	122.8 (4)
C21D—C11B—C61D	117.8 (4)	O72B—C7B—C1B	116.1 (4)
C11B—C21D—C31D	120.8 (4)	O71B—C7B—O72B	121.0 (4)
C21D—C31D—C41D	120.4 (5)	C3B—C4B—H4B	120.01
C31D—C41D—C51D	119.3 (5)	C5B—C4B—H4B	119.97
C41D—C51D—C61D	120.4 (5)	C1B—C6B—H6B	119.75
C11B—C61D—C51D	121.3 (5)	C5B—C6B—H6B	119.80

O31A—N3A—C3A—C2A	−17.8 (5)	C6A—C1A—C2A—O2A	178.7 (4)
O32A—N3A—C3A—C4A	−18.0 (5)	C7A—C1A—C2A—C3A	175.2 (3)
O31A—N3A—C3A—C4A	164.2 (4)	C6A—C1A—C2A—C3A	−3.6 (5)
O32A—N3A—C3A—C2A	160.0 (4)	C2A—C1A—C7A—O72A	−1.3 (5)
O51A—N5A—C5A—C6A	178.9 (4)	C2A—C1A—C6A—C5A	0.8 (6)
O51A—N5A—C5A—C4A	−3.7 (6)	C2A—C1A—C7A—O71A	179.6 (4)
O52A—N5A—C5A—C6A	−0.7 (6)	C6A—C1A—C7A—O72A	177.6 (4)
O52A—N5A—C5A—C4A	176.7 (4)	C7A—C1A—C2A—O2A	−2.5 (6)
O32B—N3B—C3B—C2B	−168.7 (4)	C6A—C1A—C7A—O71A	−1.4 (6)
O31B—N3B—C3B—C2B	12.3 (5)	C7A—C1A—C6A—C5A	−178.0 (3)
O32B—N3B—C3B—C4B	7.5 (5)	C1A—C2A—C3A—C4A	4.1 (5)
O31B—N3B—C3B—C4B	−171.4 (3)	O2A—C2A—C3A—N3A	3.9 (6)
O51B—N5B—C5B—C4B	3.2 (5)	C1A—C2A—C3A—N3A	−173.7 (3)
O52B—N5B—C5B—C6B	−0.3 (5)	O2A—C2A—C3A—C4A	−178.3 (4)
O52B—N5B—C5B—C4B	−177.0 (4)	N3A—C3A—C4A—C5A	176.2 (3)
O51B—N5B—C5B—C6B	179.9 (4)	C2A—C3A—C4A—C5A	−1.7 (6)
C21C—C11C—C71C—N71C	−89.6 (5)	C3A—C4A—C5A—C6A	−1.5 (6)
C21C—C11C—C71C—C81C	33.7 (6)	C3A—C4A—C5A—N5A	−178.9 (3)
C61C—C11C—C21C—C31C	−0.2 (8)	C4A—C5A—C6A—C1A	1.9 (6)
C61C—C11C—C71C—N71C	89.6 (5)	N5A—C5A—C6A—C1A	179.3 (4)
C71C—C11C—C21C—C31C	179.0 (5)	C2B—C1B—C6B—C5B	−1.0 (6)
C21C—C11C—C61C—C51C	−0.2 (7)	C7B—C1B—C2B—C3B	−175.5 (3)
C71C—C11C—C61C—C51C	−179.5 (5)	C6B—C1B—C2B—O2B	−177.8 (4)
C61C—C11C—C71C—C81C	−147.0 (5)	C6B—C1B—C2B—C3B	2.6 (5)
C11C—C21C—C31C—C41C	1.1 (9)	C7B—C1B—C2B—O2B	4.1 (6)
C21C—C31C—C41C—C51C	−1.6 (11)	C7B—C1B—C6B—C5B	177.1 (4)
C31C—C41C—C51C—C61C	1.2 (11)	C2B—C1B—C7B—O72B	−1.0 (6)
C41C—C51C—C61C—C11C	−0.2 (9)	C6B—C1B—C7B—O71B	0.5 (6)
C21D—C11B—C71D—N71D	−54.1 (5)	C6B—C1B—C7B—O72B	−179.2 (4)
C71D—C11B—C21D—C31D	179.5 (4)	C2B—C1B—C7B—O71B	178.6 (4)
C21D—C11B—C61D—C51D	0.3 (7)	C1B—C2B—C3B—C4B	−2.8 (5)
C71D—C11B—C61D—C51D	179.9 (7)	O2B—C2B—C3B—C4B	177.7 (4)
C61D—C11B—C21D—C31D	−0.9 (6)	C1B—C2B—C3B—N3B	173.2 (3)
C61D—C11B—C71D—N71D	126.3 (4)	O2B—C2B—C3B—N3B	−6.3 (6)
C21D—C11B—C71D—C81D	67.6 (5)	C2B—C3B—C4B—C5B	1.2 (6)
C61D—C11B—C71D—C81D	−112.0 (5)	N3B—C3B—C4B—C5B	−175.0 (3)
C11B—C21D—C31D—C41D	0.1 (7)	C3B—C4B—C5B—N5B	177.3 (3)
C21D—C31D—C41D—C51D	1.3 (7)	C3B—C4B—C5B—C6B	0.6 (6)
C31D—C41D—C51D—C61D	−1.9 (8)	N5B—C5B—C6B—C1B	−177.4 (3)
C41D—C51D—C61D—C11B	1.1 (8)	C4B—C5B—C6B—C1B	−0.7 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O72A—H72A···O2A	0.94 (5)	1.64 (6)	2.467 (4)	145 (5)
O72B—H72B···O2B	0.81 (4)	1.71 (4)	2.482 (4)	157 (4)
N71C—H72C···O2Aⁱ	0.94 (6)	1.98 (5)	2.840 (4)	151 (5)
N71C—H72C···O31Aⁱ	0.94 (6)	2.53 (6)	2.940 (4)	106 (4)
N71D—H72D···O71A	0.95 (6)	2.08 (6)	2.956 (5)	153 (5)
N71D—H72D···O72A	0.95 (6)	2.40 (7)	3.245 (5)	148 (5)
N71C—H73C···O71Bⁱ	0.85 (4)	2.04 (4)	2.865 (4)	161 (3)
N71D—H73D···O2B	0.92 (4)	1.94 (4)	2.824 (4)	162 (3)
N71D—H73D···O31B	0.92 (4)	2.41 (4)	3.000 (4)	122 (3)
N71C—H74C···O31Bⁱⁱ	0.93 (4)	2.17 (4)	3.099 (4)	178 (4)
N71D—H74D···O31Aⁱⁱⁱ	0.80 (4)	2.52 (3)	3.098 (5)	131 (3)
N71D—H74D···O32Aⁱⁱⁱ	0.80 (4)	2.46 (4)	3.196 (5)	153 (4)
N71D—H74D···O51B^iv	0.80 (4)	2.46 (4)	2.958 (5)	121 (3)
C31D—H31D···O52A^v	0.93	2.58	3.321 (6)	137
C71D—H71D···O31Aⁱⁱⁱ	0.98	2.55	3.245 (5)	128
C81C—H81C···O2A	0.96	2.57	3.506 (7)	164

Symmetry codes: (i) x−1, y, z; (ii) x−1, y, z+1; (iii) x, y, z−1; (iv) x, y−1, z; (v) x, y+1, z.

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