Methyl [(3,4,5-tribromo-1H-pyrrolyl-2-carbon­yl)amino]acetate 0.25-hydrate

The asymmetric unit of the title compound, C₈H₇Br₃N₂O₃·0.25H₂O, consists of two organic molecules, one water O atom and an attached H atom; the water O atom lies on a crystallographic twofold rotation axis. Inter­molecular N—H...O hydrogen-bond inter­actions link mol­ecules of the organic compound (the acetate), forming dimers. These dimers are linked by O(W)—H(W)...O and N—H...O(W) hydrogen bonds, generating a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
Some non-H atoms missing
• R factor = 0.043
• wR factor = 0.099
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level A
ABSMU01_ALERT_1_A  The ratio of given/expected absorption coefficient lies
               outside the range 0.90 <> 1.10
            Calculated value of mu =     4.934
            Value of mu given      =     9.837
CHEMW01_ALERT_1_A  The ratio of given/expected molecular weight as calculated
            from the _chemical_formula_sum lies outside
            the range 0.90 <> 1.10
            Calculated formula weight =   263.5090
            Formula weight given      =   423.3900

Alert level B
PLAT431_ALERT_2_B Short Inter HL..A Contact  Br3    ..  O5      ..       2.95 Ang.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.107     0.201
            Tmin and Tmax expected:      0.044     0.094
            RR =      1.142
            Please check that your absorption correction is appropriate.
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.25 Ratio
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.10
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.47
PLAT128_ALERT_4_C Non-standard setting of Space group P2/c    ....    P2/n
PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent .........          1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br5    ..  O3      ..       3.16 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C8 H7.5 Br1.5 N1 O1.625
            Atom count from _chemical_formula_moiety:C8 H7.5 Br3 N2 O3.25
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:C8 H7.5 Br1.5 N1 O1.625
            Atom count from the _atom_site data:  C8 H7.5 Br3 N2 O3.25
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.469
            Tmax scaled      0.094 Tmin scaled      0.050
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: Large difference may be due to a
            symmetry error - see SYMMG tests
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C8 H7.5 Br1.5 N1 O1.625
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C         64.00     64.00    0.00
           H         60.00     60.00    0.00
           Br        12.00     24.00  -12.00
           N          8.00     16.00   -8.00
           O         13.00     26.00  -13.00
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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

---

S1. Comment

Pyrrole derivatives are well known in many marine organisms (Faulkner, 2002), some show important bioactivities, such as antitumor activity (Banwell et al., 2006) and protein kinase inhibiting activity (Sosa et al., 2002). This is the reason why they have attracted our interest. This study follows our previous studies on 3-[(3,4,5-Tribromo-1H-pyrrol-2-ylcarbonyl)amino]propanoic acid (Zeng et al., 2006) and 3-Bromo-1-methyl-6,7-dihydropyrrolo[2,3-c]azepine-4,8(1H,5H)-dione (Zeng, 2006).

In the crystal structure, there are 8 molecules of Methyl [(3,4,5-tribromo-1H-pyrrole-2-carbonyl)amino]acetate and 2 crystal water molecules in each unit cell. Molecules of the acetate are linked through N—H···O H-bonds (Table 1) to form centrosymmetric dimers (Fig. 2) of graph-set motif R₂²(10) (Bernstein et al., 1995). These dimers are connected by O—H(W)···O and N—H···O(W) H-bond interactions, generating the three-dimensional network (Fig. 3). Bond lengths and angles are unexceptional.

Related literature

For related literature, see: Banwell et al. (2006); Bernstein et al. (1995); Faulkner (2002); Sosa et al. (2002); Zeng (2006); Zeng, Li, Li & Liu (2006).

S2. Experimental

The hydrochloride of glycine methyl ester (0.63 g, 5 mmol) and 3,4,5-tribromo-2-trichloroacetylpyrrole (2.25 g, 5 mmol) were added to acetonitrile (12 ml), followed by the dropwise addition of triethylamine (1.4 ml). The mixture was stirred at room temperature for 16 h and then poured into water. After filtration, the precipitate was collected as a yellow solid. The impure product was dissolved in 95% EtOH at room temperature. Colourless monoclinic crystals suitable for X-ray analysis (m.p. 470 K, 87.6% yield) grew over a period of one week when the solution was exposed to the air. CH&N elemental analysis. Calc. for C₈H_7.5Br₃N₂O_3.25: C 22.70, H 1.79, N 6.62%; found: C 22.65, H 1.83, N 6.68%.

S3. Refinement

All non-H atoms were refined with anisotropic displacement parameters. All H atoms except the H(W) were positioned geometrically [C—H = 0.97Å for CH₂, 0.96Å for CH₃, and N—H = 0.86 Å] and refined using a riding model, with U_iso = 1.2U_eq (1.5U_eq for the methyl group) of the parent atom. The H atoms attached to water O atoms in the difference Fourier maps were constrained to their parent O atoms with distance of O—H = 0.8498, and with U_iso = 1.5U_eq.

Computing details

Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Dimers & chain formed by hydrogen bonds (dashed lines).
	Fig. 3. Crystal packing of compound I and crystal water showing the three-dimensional network formed by hydrogen bonds (dashed lines).

(I)

Crystal data

C8H7Br3N2O3·0.25H2O	F(000) = 1604
Mr = 423.39	Dx = 2.287 Mg m^−3
Monoclinic, P2/n	Melting point: 470 K
Hall symbol: -P 2yac	Mo Kα radiation, λ = 0.71073 Å
a = 15.9656 (19) Å	Cell parameters from 2696 reflections
b = 9.7566 (12) Å	θ = 2.6–22.7°
c = 16.1805 (19) Å	µ = 9.84 mm^−1
β = 102.625 (2)°	T = 293 K
V = 2459.5 (5) Å^3	Prism, colourless
Z = 8	0.41 × 0.29 × 0.24 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 26.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
Tmin = 0.107, Tmax = 0.201	k = −12→11
14610 measured reflections	l = −19→17

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) = 0.099	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0272P)^2 + 4.7343P] where P = (Fo^2 + 2Fc^2)/3
4828 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.76 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br6	0.28459 (5)	0.85330 (8)	0.06071 (5)	0.0418 (2)
Br4	0.14598 (5)	0.44478 (9)	−0.19238 (5)	0.0432 (2)
Br3	0.23755 (5)	0.37740 (9)	0.37613 (5)	0.0495 (3)
Br5	0.32222 (5)	0.68636 (9)	−0.12494 (5)	0.0496 (3)
Br1	0.32381 (6)	0.02225 (10)	0.66869 (5)	0.0600 (3)
Br2	0.16429 (6)	0.26370 (10)	0.55774 (7)	0.0649 (3)
O6	0.0297 (3)	0.6921 (5)	0.3266 (3)	0.0418 (13)
N1	0.3844 (4)	0.0974 (6)	0.5250 (4)	0.0356 (16)
H1	0.4275	0.0429	0.5392	0.043*
C9	0.1664 (5)	0.5607 (7)	−0.0988 (4)	0.0316 (18)
N3	0.1121 (4)	0.5678 (6)	−0.0457 (3)	0.0328 (15)
H3	0.0665	0.5191	−0.0499	0.039*
N2	0.4197 (4)	0.2645 (6)	0.3347 (4)	0.0416 (17)
H2	0.3780	0.3223	0.3267	0.050*
O4	0.0220 (3)	0.6163 (6)	0.0733 (3)	0.0484 (15)
C13	0.0894 (5)	0.6823 (8)	0.0805 (5)	0.0301 (17)
C5	0.4292 (5)	0.1736 (8)	0.3990 (4)	0.0361 (19)
O2	0.3963 (3)	0.0869 (6)	0.1948 (3)	0.0492 (15)
C4	0.3680 (5)	0.1792 (7)	0.4544 (4)	0.0291 (17)
O1	0.4869 (3)	0.0887 (6)	0.4100 (3)	0.0503 (15)
C12	0.1402 (4)	0.6641 (7)	0.0160 (4)	0.0285 (17)
O5	0.1188 (4)	0.5676 (6)	0.2663 (3)	0.0551 (16)
O3	0.5235 (3)	0.1515 (5)	0.1720 (3)	0.0519 (16)
C15	0.0769 (5)	0.6658 (9)	0.2688 (4)	0.0358 (19)
C2	0.2633 (5)	0.2076 (8)	0.5261 (5)	0.038 (2)
C11	0.2156 (4)	0.7166 (7)	−0.0008 (4)	0.0285 (17)
N4	0.1166 (4)	0.7679 (6)	0.1437 (4)	0.0346 (15)
H4	0.1635	0.8131	0.1469	0.041*
C7	0.4587 (5)	0.1569 (8)	0.2114 (5)	0.0325 (19)
C1	0.3226 (5)	0.1157 (8)	0.5684 (5)	0.040 (2)
C10	0.2308 (4)	0.6520 (7)	−0.0732 (4)	0.0320 (18)
C16	0.0345 (6)	0.5903 (9)	0.3918 (5)	0.060 (3)
H16A	−0.0080	0.5208	0.3729	0.089*
H16B	0.0241	0.6327	0.4422	0.089*
H16C	0.0905	0.5494	0.4039	0.089*
C3	0.2933 (5)	0.2478 (7)	0.4538 (5)	0.0325 (18)
C8	0.5159 (6)	0.0477 (9)	0.1066 (5)	0.066 (3)
H8A	0.5081	−0.0404	0.1303	0.100*
H8B	0.5671	0.0468	0.0847	0.100*
H8C	0.4674	0.0680	0.0617	0.100*
C14	0.0669 (5)	0.7852 (7)	0.2076 (4)	0.0358 (19)
H14A	0.0068	0.7949	0.1802	0.043*
H14B	0.0848	0.8687	0.2390	0.043*
C6	0.4787 (5)	0.2648 (8)	0.2798 (5)	0.040 (2)
H6A	0.5362	0.2496	0.3133	0.048*
H6B	0.4777	0.3543	0.2535	0.048*
O7	0.2500	0.9820 (8)	0.2500	0.059 (2)*
H7	0.2933	1.0136	0.2337	0.37 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br6	0.0355 (5)	0.0446 (5)	0.0444 (5)	−0.0109 (4)	0.0070 (4)	−0.0039 (4)
Br4	0.0459 (5)	0.0500 (6)	0.0341 (4)	−0.0044 (4)	0.0096 (4)	−0.0073 (4)
Br3	0.0435 (5)	0.0444 (5)	0.0548 (6)	0.0136 (4)	−0.0017 (4)	−0.0009 (4)
Br5	0.0408 (5)	0.0637 (6)	0.0507 (5)	−0.0116 (5)	0.0236 (4)	−0.0056 (5)
Br1	0.0650 (6)	0.0739 (7)	0.0470 (5)	0.0008 (5)	0.0255 (5)	0.0096 (5)
Br2	0.0386 (5)	0.0773 (7)	0.0843 (7)	0.0076 (5)	0.0258 (5)	−0.0145 (6)
O6	0.036 (3)	0.052 (4)	0.042 (3)	0.004 (3)	0.018 (3)	0.000 (3)
N1	0.030 (4)	0.042 (4)	0.033 (4)	0.015 (3)	0.002 (3)	0.006 (3)
C9	0.039 (5)	0.030 (5)	0.028 (4)	0.004 (4)	0.013 (4)	0.001 (3)
N3	0.026 (3)	0.036 (4)	0.036 (4)	−0.007 (3)	0.007 (3)	0.003 (3)
N2	0.046 (4)	0.041 (4)	0.042 (4)	0.014 (3)	0.018 (3)	0.003 (3)
O4	0.036 (3)	0.063 (4)	0.052 (3)	−0.021 (3)	0.021 (3)	−0.019 (3)
C13	0.023 (4)	0.033 (5)	0.036 (4)	0.001 (4)	0.011 (4)	0.000 (4)
C5	0.041 (5)	0.040 (5)	0.027 (4)	−0.001 (4)	0.007 (4)	−0.002 (4)
O2	0.045 (4)	0.043 (4)	0.063 (4)	−0.011 (3)	0.020 (3)	−0.002 (3)
C4	0.033 (4)	0.023 (4)	0.030 (4)	0.004 (4)	0.004 (4)	−0.003 (3)
O1	0.042 (3)	0.061 (4)	0.055 (4)	0.030 (3)	0.026 (3)	0.018 (3)
C12	0.023 (4)	0.031 (5)	0.029 (4)	−0.002 (3)	0.001 (3)	0.002 (4)
O5	0.065 (4)	0.052 (4)	0.052 (4)	0.027 (3)	0.020 (3)	0.007 (3)
O3	0.051 (4)	0.057 (4)	0.056 (4)	−0.021 (3)	0.029 (3)	−0.019 (3)
C15	0.032 (5)	0.049 (6)	0.027 (4)	−0.001 (4)	0.008 (4)	−0.006 (4)
C2	0.037 (5)	0.034 (5)	0.042 (5)	0.001 (4)	0.010 (4)	−0.021 (4)
C11	0.029 (4)	0.031 (4)	0.025 (4)	−0.010 (4)	0.005 (3)	0.003 (3)
N4	0.034 (4)	0.036 (4)	0.035 (4)	−0.014 (3)	0.011 (3)	−0.013 (3)
C7	0.034 (5)	0.031 (5)	0.034 (5)	0.003 (4)	0.012 (4)	0.010 (4)
C1	0.037 (5)	0.047 (5)	0.039 (5)	0.001 (4)	0.017 (4)	−0.007 (4)
C10	0.029 (4)	0.040 (5)	0.031 (4)	−0.005 (4)	0.014 (4)	−0.003 (4)
C16	0.066 (6)	0.081 (7)	0.038 (5)	−0.008 (5)	0.024 (5)	0.005 (5)
C3	0.029 (4)	0.025 (4)	0.041 (5)	0.005 (4)	0.002 (4)	−0.007 (4)
C8	0.067 (6)	0.084 (7)	0.057 (6)	−0.020 (6)	0.033 (5)	−0.033 (5)
C14	0.040 (5)	0.037 (5)	0.033 (4)	0.002 (4)	0.013 (4)	−0.011 (4)
C6	0.047 (5)	0.038 (5)	0.038 (5)	−0.002 (4)	0.017 (4)	0.004 (4)

Geometric parameters (Å, º)

Br6—C11	1.872 (7)	C4—C3	1.367 (9)
Br4—C9	1.861 (7)	C12—C11	1.388 (9)
Br3—C3	1.866 (7)	O5—C15	1.174 (8)
Br5—C10	1.865 (7)	O3—C7	1.331 (8)
Br1—C1	1.857 (8)	O3—C8	1.450 (8)
Br2—C2	1.847 (7)	C15—C14	1.514 (10)
O6—C15	1.348 (8)	C2—C1	1.373 (10)
O6—C16	1.439 (9)	C2—C3	1.413 (10)
N1—C1	1.342 (8)	C11—C10	1.398 (9)
N1—C4	1.371 (8)	N4—C14	1.444 (8)
N1—H1	0.8600	N4—H4	0.8600
C9—N3	1.349 (8)	C7—C6	1.511 (10)
C9—C10	1.355 (9)	C16—H16A	0.9600
N3—C12	1.373 (8)	C16—H16B	0.9600
N3—H3	0.8600	C16—H16C	0.9600
N2—C5	1.350 (9)	C8—H8A	0.9600
N2—C6	1.429 (8)	C8—H8B	0.9600
N2—H2	0.8600	C8—H8C	0.9600
O4—C13	1.237 (8)	C14—H14A	0.9700
C13—N4	1.319 (8)	C14—H14B	0.9700
C13—C12	1.466 (9)	C6—H6A	0.9700
C5—O1	1.223 (8)	C6—H6B	0.9700
C5—C4	1.463 (9)	O7—H7	0.8498
O2—C7	1.189 (8)
C15—O6—C16	115.5 (6)	C14—N4—H4	120.4
C1—N1—C4	109.3 (6)	O2—C7—O3	124.8 (7)
C1—N1—H1	125.3	O2—C7—C6	126.7 (7)
C4—N1—H1	125.3	O3—C7—C6	108.5 (6)
N3—C9—C10	108.8 (6)	N1—C1—C2	109.4 (7)
N3—C9—Br4	121.8 (6)	N1—C1—Br1	121.6 (6)
C10—C9—Br4	129.4 (5)	C2—C1—Br1	129.1 (6)
C9—N3—C12	110.2 (6)	C9—C10—C11	107.0 (6)
C9—N3—H3	124.9	C9—C10—Br5	126.7 (5)
C12—N3—H3	124.9	C11—C10—Br5	126.3 (6)
C5—N2—C6	120.1 (6)	O6—C16—H16A	109.5
C5—N2—H2	119.9	O6—C16—H16B	109.5
C6—N2—H2	119.9	H16A—C16—H16B	109.5
O4—C13—N4	122.4 (7)	O6—C16—H16C	109.5
O4—C13—C12	118.4 (7)	H16A—C16—H16C	109.5
N4—C13—C12	119.3 (6)	H16B—C16—H16C	109.5
O1—C5—N2	120.7 (7)	C4—C3—C2	108.2 (7)
O1—C5—C4	121.2 (7)	C4—C3—Br3	128.5 (6)
N2—C5—C4	118.0 (7)	C2—C3—Br3	123.2 (6)
C3—C4—N1	107.3 (6)	O3—C8—H8A	109.5
C3—C4—C5	135.5 (7)	O3—C8—H8B	109.5
N1—C4—C5	117.2 (6)	H8A—C8—H8B	109.5
N3—C12—C11	105.6 (6)	O3—C8—H8C	109.5
N3—C12—C13	117.2 (6)	H8A—C8—H8C	109.5
C11—C12—C13	137.1 (7)	H8B—C8—H8C	109.5
C7—O3—C8	115.3 (6)	N4—C14—C15	112.5 (6)
O5—C15—O6	126.0 (7)	N4—C14—H14A	109.1
O5—C15—C14	125.8 (7)	C15—C14—H14A	109.1
O6—C15—C14	108.2 (7)	N4—C14—H14B	109.1
C1—C2—C3	105.8 (6)	C15—C14—H14B	109.1
C1—C2—Br2	126.4 (6)	H14A—C14—H14B	107.8
C3—C2—Br2	127.8 (6)	N2—C6—C7	113.0 (6)
C12—C11—C10	108.4 (6)	N2—C6—H6A	109.0
C12—C11—Br6	126.4 (5)	C7—C6—H6A	109.0
C10—C11—Br6	125.2 (5)	N2—C6—H6B	109.0
C13—N4—C14	119.3 (6)	C7—C6—H6B	109.0
C13—N4—H4	120.4	H6A—C6—H6B	107.8
C10—C9—N3—C12	−0.1 (8)	C4—N1—C1—Br1	−179.5 (5)
Br4—C9—N3—C12	−177.8 (5)	C3—C2—C1—N1	−1.2 (9)
C6—N2—C5—O1	−1.7 (11)	Br2—C2—C1—N1	178.1 (5)
C6—N2—C5—C4	178.8 (6)	C3—C2—C1—Br1	179.9 (6)
C1—N1—C4—C3	−1.0 (8)	Br2—C2—C1—Br1	−0.8 (11)
C1—N1—C4—C5	179.7 (6)	N3—C9—C10—C11	0.6 (8)
O1—C5—C4—C3	−171.0 (8)	Br4—C9—C10—C11	178.1 (5)
N2—C5—C4—C3	8.5 (13)	N3—C9—C10—Br5	−179.0 (5)
O1—C5—C4—N1	7.9 (11)	Br4—C9—C10—Br5	−1.5 (11)
N2—C5—C4—N1	−172.6 (6)	C12—C11—C10—C9	−0.9 (8)
C9—N3—C12—C11	−0.5 (8)	Br6—C11—C10—C9	−179.6 (5)
C9—N3—C12—C13	−178.5 (6)	C12—C11—C10—Br5	178.7 (5)
O4—C13—C12—N3	−4.0 (10)	Br6—C11—C10—Br5	0.0 (10)
N4—C13—C12—N3	176.1 (6)	N1—C4—C3—C2	0.3 (8)
O4—C13—C12—C11	178.8 (8)	C5—C4—C3—C2	179.3 (8)
N4—C13—C12—C11	−1.1 (13)	N1—C4—C3—Br3	178.5 (5)
C16—O6—C15—O5	1.9 (11)	C5—C4—C3—Br3	−2.5 (13)
C16—O6—C15—C14	−177.9 (6)	C1—C2—C3—C4	0.5 (8)
N3—C12—C11—C10	0.8 (8)	Br2—C2—C3—C4	−178.8 (5)
C13—C12—C11—C10	178.2 (8)	C1—C2—C3—Br3	−177.8 (5)
N3—C12—C11—Br6	179.5 (5)	Br2—C2—C3—Br3	2.9 (10)
C13—C12—C11—Br6	−3.1 (13)	C13—N4—C14—C15	75.8 (8)
O4—C13—N4—C14	0.5 (11)	O5—C15—C14—N4	−0.9 (11)
C12—C13—N4—C14	−179.6 (6)	O6—C15—C14—N4	178.9 (6)
C8—O3—C7—O2	−2.3 (11)	C5—N2—C6—C7	81.4 (9)
C8—O3—C7—C6	177.3 (6)	O2—C7—C6—N2	8.7 (11)
C4—N1—C1—C2	1.4 (9)	O3—C7—C6—N2	−170.9 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O7	0.86	2.53	3.202 (8)	136
O7—H7···O2^i	0.85	2.02	2.866 (6)	180
N3—H3···O4^ii	0.86	1.91	2.756 (8)	167
N1—H1···O1^iii	0.86	1.92	2.772 (8)	168

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