Brucinium hydrogen N-(4-nitro­benzo­yl)-l-aspartate dihydrate

Białońska, A.; Ciunik, Z.

doi:10.1107/S1600536807013244

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Brucinium hydrogen N-(4-nitrobenzoyl)-L-aspartate dihydrate

A. Białońska and Z. Ciunik

In the title compound, C₂₃H₂₇N₂O₄⁺·C₁₁H₉N₂O₇⁻·2H₂O, nitro

π stacking interactions are formed between the nitro group of the aspartic acid derivative and the arene rings projecting out of brucinium columns. The protonated amine N atom of the brucinium cation forms an N—H⁺

O⁻ hydrogen bond to the β-carboxyl group of the anion. The α- and β-carboxyl groups of the anions are linked by short hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807013244/hg2210sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807013244/hg2210Isup2.hkl Contains datablock I

CCDC reference: 643650

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.009 Å
H-atom completeness 98%
R factor = 0.083
wR factor = 0.193
Data-to-parameter ratio = 7.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT430_ALERT_2_A Short Inter D...A Contact  O6     ..  O8      ..       2.46 Ang.

Author Response: H-atom linked to carboxyl group is not determined (probably the H-atom is disordered). The carboxyl O6 and O8(x-1, y, z) atoms are probably linked to each other by very short hydrogen bonds.


Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.117
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.82
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C25    -   C26     ..       5.98 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C26
PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........         O6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C34 H40 N4 O13
            Atom count from the _atom_site data:  C34 H39 N4 O13
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C34 H40 N4 O13
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        136.00    136.00    0.00
           H        160.00    156.00    4.00
           N         16.00     16.00    0.00
           O         52.00     52.00    0.00
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           25.99
           From the CIF: _reflns_number_total               3595
           Count of symmetry unique reflns         3619
           Completeness (_total/calc)             99.34%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of N2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C19    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C25    = .          S

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

  13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 1999) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.

Brucinium hydrogen N-(4-nitrobenzoyl)-L-aspartate dihydrate top

Crystal data top

C₂₃H₂₇N₂O₄⁺·C₁₁H₉N₂O₇⁻·2H₂O	D_x = 1.467 Mg m⁻³
M_r = 712.70	Melting point = 446–449 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12256 reflections
a = 7.435 (2) Å	θ = 3.4–28.5°
b = 12.168 (3) Å	µ = 0.11 mm⁻¹
c = 35.664 (4) Å	T = 100 K
V = 3226.5 (12) Å³	Plate, orange
Z = 4	0.30 × 0.30 × 0.10 mm
F(000) = 1504

Data collection top

Kuma KM-4 CCD area-detector diffractometer	2569 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.117
Graphite monochromator	θ_max = 26.0°, θ_min = 3.4°
ω scans	h = −9→7
20076 measured reflections	k = −15→14
3595 independent reflections	l = −43→42

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.193	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0915P)²] where P = (F_o² + 2F_c²)/3
3595 reflections	(Δ/σ)_max < 0.001
460 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	1.1337 (6)	−0.0183 (4)	0.04199 (12)	0.0259 (11)
O2	0.9635 (6)	0.6957 (3)	0.05630 (12)	0.0286 (11)
O3	0.9530 (6)	0.6774 (4)	0.12907 (12)	0.0282 (11)
O4	1.1220 (6)	0.3386 (4)	−0.01078 (12)	0.0295 (11)
N1	1.0149 (7)	0.2906 (4)	0.04749 (14)	0.0212 (12)
N2	0.9557 (8)	0.1309 (5)	0.16437 (15)	0.0297 (14)
H2	0.9264	0.1465	0.1892	0.036*
C1	0.9933 (8)	0.4990 (5)	0.04718 (17)	0.0227 (14)
H1	1.0040	0.5056	0.0207	0.027*
C2	0.9737 (8)	0.5912 (5)	0.06971 (18)	0.0226 (14)
C3	0.9627 (9)	0.5802 (6)	0.10914 (19)	0.0275 (15)
C4	0.9596 (9)	0.4762 (5)	0.12499 (18)	0.0240 (14)
H4	0.9448	0.4682	0.1513	0.029*
C5	0.9781 (8)	0.3845 (5)	0.10271 (17)	0.0213 (14)
C6	0.9969 (8)	0.3968 (5)	0.06448 (18)	0.0213 (14)
C7	0.9585 (9)	0.2653 (6)	0.11290 (16)	0.0240 (15)
C8	1.0199 (8)	0.2031 (5)	0.07681 (17)	0.0210 (14)
H8	0.9310	0.1443	0.0705	0.025*
C9	1.0898 (9)	0.2662 (6)	0.01309 (18)	0.0272 (16)
C10	1.1274 (9)	0.1482 (6)	0.00742 (18)	0.0266 (15)
H10A	1.2019	0.1405	−0.0154	0.032*
H10B	1.0117	0.1105	0.0025	0.032*
C11	1.2238 (9)	0.0869 (5)	0.03987 (18)	0.0263 (15)
H11	1.3533	0.0756	0.0334	0.032*
C12	1.2160 (9)	−0.0925 (5)	0.06875 (17)	0.0256 (15)
H12A	1.3460	−0.0760	0.0709	0.031*
H12B	1.2031	−0.1692	0.0599	0.031*
C13	1.1293 (9)	−0.0808 (6)	0.10611 (19)	0.0296 (16)
H13	1.0588	−0.1396	0.1157	0.036*
C14	1.1482 (9)	0.0102 (5)	0.12640 (18)	0.0270 (15)
C15	1.0593 (10)	0.0260 (5)	0.16395 (19)	0.0295 (16)
H15A	0.9773	−0.0364	0.1690	0.035*
H15B	1.1519	0.0275	0.1839	0.035*
C16	0.7803 (10)	0.1237 (6)	0.14214 (18)	0.0317 (17)
H16A	0.6772	0.1086	0.1589	0.038*
H16B	0.7870	0.0651	0.1229	0.038*
C17	0.7623 (9)	0.2361 (6)	0.12394 (18)	0.0257 (15)
H17A	0.7128	0.2906	0.1418	0.031*
H17B	0.6837	0.2329	0.1016	0.031*
C18	1.2091 (9)	0.1562 (6)	0.07581 (18)	0.0258 (15)
H18	1.2908	0.2204	0.0720	0.031*
C19	1.2656 (9)	0.1045 (5)	0.11346 (16)	0.0220 (14)
H19	1.3925	0.0779	0.1113	0.026*
C20	1.2584 (9)	0.1979 (6)	0.14264 (19)	0.0295 (16)
H20A	1.3122	0.1730	0.1666	0.035*
H20B	1.3275	0.2621	0.1335	0.035*
C21	1.0625 (9)	0.2299 (5)	0.14871 (18)	0.0258 (15)
H21	1.0573	0.2912	0.1674	0.031*
C22	0.9476 (11)	0.7075 (6)	0.01610 (18)	0.0334 (17)
H22A	0.9414	0.7857	0.0096	0.050*
H22B	0.8380	0.6705	0.0075	0.050*
H22C	1.0525	0.6743	0.0039	0.050*
C23	0.9309 (10)	0.6691 (6)	0.16849 (19)	0.0329 (17)
H23A	0.9261	0.7429	0.1794	0.049*
H23B	1.0326	0.6286	0.1792	0.049*
H23C	0.8188	0.6300	0.1740	0.049*
O5	0.2271 (7)	0.4415 (5)	0.20310 (16)	0.0540 (16)
O6	0.1541 (7)	0.4258 (6)	0.26263 (15)	0.0624 (18)
O7	0.8567 (8)	0.2622 (6)	0.22599 (16)	0.0608 (17)
O8	0.8395 (8)	0.4420 (5)	0.24227 (18)	0.0590 (18)
O9	0.5177 (7)	0.4600 (4)	0.32310 (14)	0.0412 (14)
O10	0.5388 (9)	0.0590 (4)	0.45995 (15)	0.0540 (16)
O11	0.5603 (8)	−0.0686 (4)	0.41725 (15)	0.0473 (14)
N3	0.4717 (8)	0.3278 (5)	0.27899 (16)	0.0387 (15)
H3	0.4618	0.2568	0.2749	0.046*
N4	0.5437 (9)	0.0278 (5)	0.42726 (18)	0.0367 (15)
C24	0.2680 (10)	0.4260 (8)	0.2349 (2)	0.046 (2)
C25	0.4604 (10)	0.4027 (8)	0.2470 (2)	0.044 (2)
H25	0.5139	0.4742	0.2551	0.053*
C26	0.5774 (13)	0.3584 (9)	0.2159 (2)	0.065 (3)
H26A	0.5666	0.4064	0.1936	0.078*
H26B	0.5357	0.2840	0.2088	0.078*
C27	0.7727 (10)	0.3530 (8)	0.2280 (2)	0.048 (2)
C28	0.4968 (9)	0.3631 (7)	0.31455 (19)	0.0326 (17)
C29	0.5077 (9)	0.2728 (6)	0.34297 (18)	0.0291 (16)
C30	0.4456 (9)	0.2947 (6)	0.37960 (18)	0.0294 (16)
H30	0.3964	0.3647	0.3854	0.035*
C31	0.4561 (10)	0.2148 (6)	0.40699 (19)	0.0322 (17)
H31	0.4149	0.2293	0.4317	0.039*
C32	0.5275 (9)	0.1134 (6)	0.39782 (18)	0.0282 (16)
C33	0.5866 (10)	0.0875 (6)	0.36215 (19)	0.0347 (17)
H33	0.6322	0.0165	0.3565	0.042*
C34	0.5770 (9)	0.1696 (6)	0.33466 (19)	0.0338 (17)
H34	0.6185	0.1545	0.3100	0.041*
O1W	1.2229 (6)	0.5300 (4)	−0.05196 (13)	0.0356 (12)
H11W	1.3376	0.5264	−0.0491	0.053*
H12W	1.2164	0.4730	−0.0377	0.053*
O2W	0.7762 (9)	0.6678 (5)	0.25600 (15)	0.0619 (18)
H21W	0.8802	0.6949	0.2611	0.093*
H22W	0.7954	0.5991	0.2519	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.021 (2)	0.022 (2)	0.035 (3)	−0.001 (2)	−0.004 (2)	0.005 (2)
O2	0.034 (3)	0.024 (3)	0.028 (3)	0.002 (2)	−0.007 (2)	0.0009 (19)
O3	0.036 (3)	0.020 (2)	0.029 (3)	−0.001 (2)	−0.002 (2)	−0.0068 (19)
O4	0.029 (3)	0.030 (3)	0.029 (3)	0.001 (2)	0.005 (2)	0.005 (2)
N1	0.019 (3)	0.021 (3)	0.024 (3)	−0.003 (2)	−0.003 (2)	0.001 (2)
N2	0.031 (3)	0.040 (4)	0.019 (3)	0.000 (3)	0.002 (3)	−0.001 (3)
C1	0.023 (3)	0.024 (3)	0.021 (3)	0.005 (3)	−0.005 (3)	−0.002 (3)
C2	0.019 (3)	0.019 (3)	0.030 (4)	0.000 (3)	−0.003 (3)	0.006 (3)
C3	0.019 (3)	0.027 (4)	0.036 (4)	0.000 (3)	−0.005 (3)	−0.004 (3)
C4	0.022 (3)	0.021 (3)	0.029 (4)	0.005 (3)	0.001 (3)	0.002 (3)
C5	0.019 (3)	0.018 (3)	0.026 (3)	−0.005 (3)	0.000 (3)	0.002 (3)
C6	0.012 (3)	0.021 (3)	0.030 (4)	−0.002 (3)	0.002 (3)	−0.001 (3)
C7	0.021 (3)	0.035 (4)	0.017 (3)	0.002 (3)	−0.004 (3)	0.005 (3)
C8	0.018 (3)	0.023 (3)	0.021 (3)	−0.003 (3)	0.000 (3)	0.001 (3)
C9	0.021 (4)	0.036 (4)	0.025 (4)	0.002 (3)	0.003 (3)	0.001 (3)
C10	0.029 (4)	0.026 (4)	0.024 (4)	0.002 (3)	0.008 (3)	−0.004 (3)
C11	0.023 (3)	0.021 (4)	0.035 (4)	0.000 (3)	0.005 (3)	−0.002 (3)
C12	0.021 (3)	0.024 (4)	0.032 (4)	−0.003 (3)	−0.009 (3)	0.008 (3)
C13	0.024 (4)	0.020 (4)	0.045 (4)	−0.002 (3)	−0.003 (3)	0.005 (3)
C14	0.030 (4)	0.022 (4)	0.029 (4)	0.000 (3)	−0.009 (3)	0.010 (3)
C15	0.036 (4)	0.017 (3)	0.036 (4)	−0.004 (3)	−0.005 (3)	0.012 (3)
C16	0.030 (4)	0.035 (4)	0.031 (4)	−0.007 (3)	0.005 (3)	−0.004 (3)
C17	0.020 (3)	0.030 (4)	0.027 (4)	−0.001 (3)	0.002 (3)	0.000 (3)
C18	0.019 (3)	0.023 (4)	0.035 (4)	−0.003 (3)	0.003 (3)	0.003 (3)
C19	0.022 (3)	0.021 (3)	0.022 (3)	−0.004 (3)	−0.008 (3)	0.003 (3)
C20	0.028 (4)	0.032 (4)	0.029 (4)	−0.003 (3)	−0.006 (3)	−0.003 (3)
C21	0.029 (4)	0.025 (4)	0.024 (3)	−0.012 (3)	0.003 (3)	0.006 (3)
C22	0.041 (4)	0.026 (4)	0.033 (4)	0.003 (3)	−0.005 (3)	0.004 (3)
C23	0.035 (4)	0.025 (4)	0.039 (4)	0.005 (3)	0.000 (3)	−0.010 (3)
O5	0.038 (3)	0.072 (4)	0.051 (4)	−0.009 (3)	−0.007 (3)	0.020 (3)
O6	0.032 (3)	0.105 (5)	0.051 (4)	0.014 (4)	0.002 (3)	0.003 (4)
O7	0.038 (3)	0.084 (5)	0.060 (4)	0.002 (4)	0.016 (3)	−0.017 (4)
O8	0.034 (3)	0.062 (4)	0.080 (5)	0.000 (3)	−0.004 (3)	−0.022 (4)
O9	0.041 (3)	0.030 (3)	0.053 (3)	0.008 (3)	0.006 (3)	0.002 (3)
O10	0.083 (4)	0.039 (3)	0.040 (3)	0.000 (3)	0.015 (3)	0.001 (3)
O11	0.057 (4)	0.035 (3)	0.051 (3)	0.001 (3)	0.003 (3)	−0.001 (3)
N3	0.046 (4)	0.041 (4)	0.029 (3)	−0.002 (3)	−0.002 (3)	0.004 (3)
N4	0.039 (4)	0.031 (4)	0.040 (4)	−0.010 (3)	0.012 (3)	−0.001 (3)
C24	0.027 (4)	0.073 (6)	0.036 (5)	−0.008 (4)	0.001 (4)	0.005 (5)
C25	0.030 (4)	0.062 (6)	0.039 (4)	0.007 (4)	0.011 (3)	0.001 (4)
C26	0.064 (6)	0.083 (7)	0.049 (6)	−0.018 (6)	−0.011 (5)	−0.001 (5)
C27	0.021 (4)	0.067 (6)	0.055 (5)	0.016 (4)	0.010 (4)	−0.004 (5)
C28	0.022 (4)	0.048 (5)	0.028 (4)	0.004 (3)	0.000 (3)	0.005 (3)
C29	0.022 (4)	0.034 (4)	0.031 (4)	−0.001 (3)	−0.002 (3)	−0.003 (3)
C30	0.020 (4)	0.041 (4)	0.027 (4)	0.006 (3)	−0.004 (3)	−0.007 (3)
C31	0.031 (4)	0.041 (4)	0.025 (4)	−0.008 (3)	0.004 (3)	−0.006 (3)
C32	0.023 (4)	0.040 (4)	0.022 (4)	−0.003 (3)	−0.004 (3)	−0.002 (3)
C33	0.028 (4)	0.038 (4)	0.038 (4)	0.002 (3)	0.001 (3)	−0.005 (4)
C34	0.029 (4)	0.048 (5)	0.025 (4)	0.007 (4)	0.001 (3)	−0.009 (3)
O1W	0.030 (3)	0.033 (3)	0.044 (3)	0.008 (2)	−0.004 (2)	0.007 (2)
O2W	0.062 (4)	0.063 (4)	0.061 (4)	0.011 (4)	0.000 (3)	0.005 (3)

Geometric parameters (Å, º) top

O1—C12	1.450 (7)	C17—H17B	0.9900
O1—C11	1.446 (8)	C18—C19	1.541 (8)
O2—C2	1.362 (7)	C18—H18	1.0000
O2—C22	1.445 (7)	C19—C20	1.543 (9)
O3—C3	1.382 (8)	C19—H19	1.0000
O3—C23	1.419 (8)	C20—C21	1.523 (10)
O4—C9	1.249 (8)	C20—H20A	0.9900
N1—C9	1.380 (8)	C20—H20B	0.9900
N1—C6	1.433 (8)	C21—H21	1.0000
N1—C8	1.493 (8)	C22—H22A	0.9800
N2—C15	1.491 (9)	C22—H22B	0.9800
N2—C16	1.529 (9)	C22—H22C	0.9800
N2—C21	1.547 (8)	C23—H23A	0.9800
N2—H2	0.9300	C23—H23B	0.9800
C1—C2	1.388 (9)	C23—H23C	0.9800
C1—C6	1.389 (9)	O5—C24	1.188 (9)
C1—H1	0.9500	O6—C24	1.302 (9)
C2—C3	1.415 (9)	O7—C27	1.271 (10)
C3—C4	1.387 (9)	O8—C27	1.296 (10)
C4—C5	1.376 (9)	O9—C28	1.228 (9)
C4—H4	0.9500	O10—N4	1.227 (7)
C5—C6	1.378 (9)	O11—N4	1.233 (8)
C5—C7	1.503 (9)	N3—C28	1.352 (9)
C7—C17	1.552 (9)	N3—C25	1.463 (9)
C7—C21	1.554 (9)	N3—H3	0.8800
C7—C8	1.561 (9)	N4—C32	1.484 (9)
C8—C18	1.518 (9)	C24—C25	1.521 (11)
C8—H8	1.0000	C25—C26	1.509 (12)
C9—C10	1.477 (10)	C25—H25	1.0000
C10—C11	1.552 (9)	C26—C27	1.517 (12)
C10—H10A	0.9900	C26—H26A	0.9900
C10—H10B	0.9900	C26—H26B	0.9900
C11—C18	1.538 (9)	C28—C29	1.497 (10)
C11—H11	1.0000	C29—C34	1.389 (10)
C12—C13	1.487 (9)	C29—C30	1.411 (9)
C12—H12A	0.9900	C30—C31	1.380 (10)
C12—H12B	0.9900	C30—H30	0.9500
C13—C14	1.331 (9)	C31—C32	1.383 (10)
C13—H13	0.9500	C31—H31	0.9500
C14—C15	1.505 (9)	C32—C33	1.382 (9)
C14—C19	1.514 (9)	C33—C34	1.401 (10)
C15—H15A	0.9900	C33—H33	0.9500
C15—H15B	0.9900	C34—H34	0.9500
C16—C17	1.520 (9)	O1W—H11W	0.8600
C16—H16A	0.9900	O1W—H12W	0.8601
C16—H16B	0.9900	O2W—H21W	0.8599
C17—H17A	0.9900	O2W—H22W	0.8600

C12—O1—C11	113.0 (5)	C7—C17—H17B	111.1
C2—O2—C22	116.5 (5)	H17A—C17—H17B	109.1
C3—O3—C23	117.0 (5)	C8—C18—C11	107.0 (5)
C9—N1—C6	127.5 (5)	C8—C18—C19	112.7 (5)
C9—N1—C8	117.3 (5)	C11—C18—C19	118.9 (5)
C6—N1—C8	110.4 (5)	C8—C18—H18	105.8
C15—N2—C16	112.7 (5)	C11—C18—H18	105.8
C15—N2—C21	113.5 (5)	C19—C18—H18	105.8
C16—N2—C21	107.2 (5)	C14—C19—C20	109.4 (5)
C15—N2—H2	107.7	C14—C19—C18	114.7 (5)
C16—N2—H2	107.7	C20—C19—C18	106.1 (5)
C21—N2—H2	107.7	C14—C19—H19	108.8
C2—C1—C6	117.9 (6)	C20—C19—H19	108.8
C2—C1—H1	121.0	C18—C19—H19	108.8
C6—C1—H1	121.0	C21—C20—C19	108.5 (5)
O2—C2—C1	123.9 (6)	C21—C20—H20A	110.0
O2—C2—C3	115.7 (6)	C19—C20—H20A	110.0
C1—C2—C3	120.4 (6)	C21—C20—H20B	110.0
O3—C3—C4	124.8 (6)	C19—C20—H20B	110.0
O3—C3—C2	115.7 (6)	H20A—C20—H20B	108.4
C4—C3—C2	119.5 (6)	C20—C21—N2	110.1 (5)
C5—C4—C3	120.2 (6)	C20—C21—C7	115.4 (5)
C5—C4—H4	119.9	N2—C21—C7	104.9 (5)
C3—C4—H4	119.9	C20—C21—H21	108.7
C6—C5—C4	119.6 (6)	N2—C21—H21	108.7
C6—C5—C7	110.7 (5)	C7—C21—H21	108.7
C4—C5—C7	129.3 (6)	O2—C22—H22A	109.5
C5—C6—C1	122.3 (6)	O2—C22—H22B	109.5
C5—C6—N1	109.3 (5)	H22A—C22—H22B	109.5
C1—C6—N1	128.4 (6)	O2—C22—H22C	109.5
C5—C7—C17	111.9 (6)	H22A—C22—H22C	109.5
C5—C7—C21	114.8 (5)	H22B—C22—H22C	109.5
C17—C7—C21	101.3 (5)	O3—C23—H23A	109.5
C5—C7—C8	103.9 (5)	O3—C23—H23B	109.5
C17—C7—C8	111.9 (5)	H23A—C23—H23B	109.5
C21—C7—C8	113.5 (5)	O3—C23—H23C	109.5
N1—C8—C18	106.0 (5)	H23A—C23—H23C	109.5
N1—C8—C7	103.0 (5)	H23B—C23—H23C	109.5
C18—C8—C7	118.2 (5)	C28—N3—C25	122.9 (7)
N1—C8—H8	109.7	C28—N3—H3	118.6
C18—C8—H8	109.7	C25—N3—H3	118.6
C7—C8—H8	109.7	O10—N4—O11	124.9 (6)
O4—C9—N1	122.1 (6)	O10—N4—C32	117.0 (6)
O4—C9—C10	123.8 (6)	O11—N4—C32	118.1 (6)
N1—C9—C10	114.1 (6)	O5—C24—O6	124.0 (7)
C9—C10—C11	116.9 (6)	O5—C24—C25	122.7 (7)
C9—C10—H10A	108.1	O6—C24—C25	113.3 (7)
C11—C10—H10A	108.1	N3—C25—C26	108.6 (7)
C9—C10—H10B	108.1	N3—C25—C24	113.1 (6)
C11—C10—H10B	108.1	C26—C25—C24	113.6 (7)
H10A—C10—H10B	107.3	N3—C25—H25	107.1
O1—C11—C18	114.1 (5)	C26—C25—H25	107.1
O1—C11—C10	104.5 (5)	C24—C25—H25	107.1
C18—C11—C10	109.0 (5)	C25—C26—C27	110.9 (7)
O1—C11—H11	109.7	C25—C26—H26A	109.5
C18—C11—H11	109.7	C27—C26—H26A	109.5
C10—C11—H11	109.7	C25—C26—H26B	109.5
O1—C12—C13	110.3 (5)	C27—C26—H26B	109.5
O1—C12—H12A	109.6	H26A—C26—H26B	108.0
C13—C12—H12A	109.6	O8—C27—O7	124.1 (7)
O1—C12—H12B	109.6	O8—C27—C26	116.3 (8)
C13—C12—H12B	109.6	O7—C27—C26	119.5 (9)
H12A—C12—H12B	108.1	O9—C28—N3	123.7 (7)
C14—C13—C12	121.4 (6)	O9—C28—C29	122.0 (6)
C14—C13—H13	119.3	N3—C28—C29	114.2 (7)
C12—C13—H13	119.3	C34—C29—C30	119.3 (6)
C13—C14—C15	122.9 (6)	C34—C29—C28	122.6 (6)
C13—C14—C19	121.7 (6)	C30—C29—C28	118.1 (6)
C15—C14—C19	115.3 (5)	C31—C30—C29	120.3 (7)
N2—C15—C14	110.2 (5)	C31—C30—H30	119.9
N2—C15—H15A	109.6	C29—C30—H30	119.9
C14—C15—H15A	109.6	C30—C31—C32	118.8 (6)
N2—C15—H15B	109.6	C30—C31—H31	120.6
C14—C15—H15B	109.6	C32—C31—H31	120.6
H15A—C15—H15B	108.1	C31—C32—C33	122.9 (7)
N2—C16—C17	104.2 (5)	C31—C32—N4	119.4 (6)
N2—C16—H16A	110.9	C33—C32—N4	117.7 (6)
C17—C16—H16A	110.9	C32—C33—C34	117.7 (7)
N2—C16—H16B	110.9	C32—C33—H33	121.1
C17—C16—H16B	110.9	C34—C33—H33	121.1
H16A—C16—H16B	108.9	C33—C34—C29	120.9 (6)
C16—C17—C7	103.4 (5)	C33—C34—H34	119.5
C16—C17—H17A	111.1	C29—C34—H34	119.5
C7—C17—H17A	111.1	H11W—O1W—H12W	86.9
C16—C17—H17B	111.1	H21W—O2W—H22W	105.0

C22—O2—C2—C1	8.8 (9)	C21—C7—C17—C16	−43.7 (6)
C22—O2—C2—C3	−171.1 (6)	C8—C7—C17—C16	77.5 (6)
C6—C1—C2—O2	−178.3 (6)	N1—C8—C18—C11	−72.8 (6)
C6—C1—C2—C3	1.6 (9)	C7—C8—C18—C11	172.4 (5)
C23—O3—C3—C4	−2.7 (9)	N1—C8—C18—C19	154.7 (5)
C23—O3—C3—C2	176.3 (5)	C7—C8—C18—C19	40.0 (8)
O2—C2—C3—O3	−3.4 (8)	O1—C11—C18—C8	−75.7 (6)
C1—C2—C3—O3	176.7 (6)	C10—C11—C18—C8	40.7 (7)
O2—C2—C3—C4	175.7 (6)	O1—C11—C18—C19	53.3 (7)
C1—C2—C3—C4	−4.3 (9)	C10—C11—C18—C19	169.7 (6)
O3—C3—C4—C5	−177.1 (6)	C13—C14—C19—C20	179.4 (6)
C2—C3—C4—C5	3.9 (10)	C15—C14—C19—C20	−2.0 (7)
C3—C4—C5—C6	−1.0 (9)	C13—C14—C19—C18	60.3 (8)
C3—C4—C5—C7	−172.5 (6)	C15—C14—C19—C18	−121.1 (6)
C4—C5—C6—C1	−1.7 (9)	C8—C18—C19—C14	60.2 (7)
C7—C5—C6—C1	171.3 (6)	C11—C18—C19—C14	−66.2 (8)
C4—C5—C6—N1	179.6 (6)	C8—C18—C19—C20	−60.8 (7)
C7—C5—C6—N1	−7.4 (7)	C11—C18—C19—C20	172.9 (5)
C2—C1—C6—C5	1.4 (9)	C14—C19—C20—C21	−55.4 (7)
C2—C1—C6—N1	179.7 (6)	C18—C19—C20—C21	68.8 (7)
C9—N1—C6—C5	−158.3 (6)	C19—C20—C21—N2	61.8 (7)
C8—N1—C6—C5	−3.8 (7)	C19—C20—C21—C7	−56.8 (7)
C9—N1—C6—C1	23.1 (10)	C15—N2—C21—C20	−9.2 (7)
C8—N1—C6—C1	177.6 (6)	C16—N2—C21—C20	−134.3 (5)
C6—C5—C7—C17	−106.0 (6)	C15—N2—C21—C7	115.6 (6)
C4—C5—C7—C17	66.1 (9)	C16—N2—C21—C7	−9.5 (7)
C6—C5—C7—C21	139.3 (6)	C5—C7—C21—C20	−85.8 (7)
C4—C5—C7—C21	−48.5 (9)	C17—C7—C21—C20	153.5 (6)
C6—C5—C7—C8	14.9 (7)	C8—C7—C21—C20	33.5 (8)
C4—C5—C7—C8	−173.0 (6)	C5—C7—C21—N2	152.9 (5)
C9—N1—C8—C18	45.2 (7)	C17—C7—C21—N2	32.2 (6)
C6—N1—C8—C18	−112.2 (6)	C8—C7—C21—N2	−87.9 (6)
C9—N1—C8—C7	170.0 (5)	C28—N3—C25—C26	133.8 (8)
C6—N1—C8—C7	12.6 (6)	C28—N3—C25—C24	−99.2 (9)
C5—C7—C8—N1	−15.9 (6)	O5—C24—C25—N3	−146.6 (9)
C17—C7—C8—N1	105.0 (5)	O6—C24—C25—N3	32.6 (11)
C21—C7—C8—N1	−141.2 (5)	O5—C24—C25—C26	−22.2 (14)
C5—C7—C8—C18	100.4 (6)	O6—C24—C25—C26	156.9 (8)
C17—C7—C8—C18	−138.7 (6)	N3—C25—C26—C27	−61.7 (10)
C21—C7—C8—C18	−24.8 (8)	C24—C25—C26—C27	171.5 (8)
C6—N1—C9—O4	−13.7 (10)	C25—C26—C27—O8	−51.3 (11)
C8—N1—C9—O4	−166.7 (6)	C25—C26—C27—O7	124.4 (9)
C6—N1—C9—C10	166.2 (6)	C25—N3—C28—O9	−2.3 (11)
C8—N1—C9—C10	13.3 (8)	C25—N3—C28—C29	−179.0 (6)
O4—C9—C10—C11	133.2 (7)	O9—C28—C29—C34	−145.4 (7)
N1—C9—C10—C11	−46.8 (8)	N3—C28—C29—C34	31.3 (10)
C12—O1—C11—C18	−66.4 (7)	O9—C28—C29—C30	34.2 (10)
C12—O1—C11—C10	174.7 (5)	N3—C28—C29—C30	−149.1 (6)
C9—C10—C11—O1	139.1 (6)	C34—C29—C30—C31	0.9 (10)
C9—C10—C11—C18	16.7 (8)	C28—C29—C30—C31	−178.7 (6)
C11—O1—C12—C13	91.8 (6)	C29—C30—C31—C32	−0.3 (10)
O1—C12—C13—C14	−68.2 (8)	C30—C31—C32—C33	−1.1 (11)
C12—C13—C14—C15	178.7 (6)	C30—C31—C32—N4	178.5 (6)
C12—C13—C14—C19	−2.9 (10)	O10—N4—C32—C31	−19.1 (10)
C16—N2—C15—C14	74.8 (7)	O11—N4—C32—C31	160.7 (7)
C21—N2—C15—C14	−47.3 (7)	O10—N4—C32—C33	160.5 (6)
C13—C14—C15—N2	−127.2 (7)	O11—N4—C32—C33	−19.8 (9)
C19—C14—C15—N2	54.3 (7)	C31—C32—C33—C34	1.7 (10)
C15—N2—C16—C17	−143.3 (5)	N4—C32—C33—C34	−177.9 (6)
C21—N2—C16—C17	−17.8 (6)	C32—C33—C34—C29	−1.0 (11)
N2—C16—C17—C7	38.3 (6)	C30—C29—C34—C33	−0.3 (11)
C5—C7—C17—C16	−166.4 (5)	C28—C29—C34—C33	179.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O7	0.93	1.99	2.815 (8)	146
N3—H3···O2Wⁱ	0.88	2.35	2.958 (9)	126
O1W—H11W···O1ⁱⁱ	0.86	2.22	3.078 (6)	180
O1W—H12W···O4	0.86	2.02	2.853 (7)	162
O2W—H21W···O7ⁱⁱⁱ	0.86	2.17	3.030 (9)	180
O2W—H22W···O8	0.86	1.97	2.830 (9)	180

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

Nitro···π interactions (Å,°). Cg1 represents the centroid of the brucinium arene ring C1–C6 top

Nitro	Cg1	Nitro···Cg1	Interplanar angle	Nitro (perp)	Cg1 (perp)	Slippage
N4	Cg1^v	3.935 (6)	10.5 (2)	3.872 (7)	3.902	0.701
N4	Cg1^vi	3.626 (6)	10.5 (2)	3.522 (7)	3.491	0.862

Nitro···Cg is the distance between the N atom of the nitro group and the ring centroid. The interplanar angle is that between the planes of the nitro group and ring Cg1. Nitro (perp) is the perpendicular distance of atom N4 from the ring. Cg1 (perp) is the perpendicular distance of Cg1 from the nitro group. Symmetry code: (v) 1-x, -1/2+y, 1/2-z, (vi) 2-x, -1/2+y, 1/2-z.

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