2-[Bis(2-bromo­ethyl)amino]-N-(2-hydroxy­ethyl)-3,5-dinitro­benzamide

The title compound, C₁₃H₁₆Br₂N₄O₆, is a dinitro­benzamide dibromo mustard. The tetra­substituted benzene ring is significantly distorted from both planarity and ideal hexagonal symmetry. The mol­ecules assemble in the crystal structure via hydrogen-bonding inter­actions between the amide groups on adjacent mol­ecules, and by O—H...O(nitro) and O—H...Br contacts. There are short Br...Br contacts (3.388 Å) that are significantly less than the sum of the van der Waals radii of two Br atoms.

Key indicators

• Single-crystal X-ray study
• T = 86 K
• Mean [sigma](Wave) = 0.000 Å
• R factor = 0.016
• wR factor = 0.038
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level G
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      0.792
            Tmax scaled      0.436 Tmin scaled      0.310
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           26.41
           From the CIF: _reflns_number_total               3643
           Count of symmetry unique reflns         2099
           Completeness (_total/calc)            173.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1544
           Fraction of Friedel pairs measured     0.736
           Are heavy atom types Z>Si present        yes

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

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

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-[Bis(2-bromoethyl)amino]-N-(2-hydroxyethyl)-3,5-dinitrobenzamide

Crystal data

C13H16Br2N4O6	Dx = 1.812 Mg m^−3
Mr = 484.10	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8192 reflections
a = 9.2950 (1) Å	θ = 2.1–26.4°
b = 9.9641 (2) Å	µ = 4.61 mm^−1
c = 19.1575 (2) Å	T = 86 K
V = 1774.30 (4) Å^3	Block, yellow
Z = 4	0.4 × 0.18 × 0.18 mm
F(000) = 960

Data collection

Siemens SMART CCD diffractometer	3643 independent reflections
Radiation source: fine-focus sealed tube	3541 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Area–detector ω scans	θmax = 26.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→11
Tmin = 0.391, Tmax = 0.551	k = −12→11
10742 measured reflections	l = −22→23

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.016	H-atom parameters constrained
wR(F^2) = 0.038	w = 1/[σ^2(Fo^2) + (0.0164P)^2 + 0.6655P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.002
3643 reflections	Δρmax = 0.25 e Å^−3
227 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1548 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.007 (5)

Special details

Experimental. ¹H NMR [(CD₃)₂SO]: δ 8.74 (d, J = 2.7 Hz, 1H), 8.73 (m, 1H), 8.34 (d, J = 2.7 Hz, 1H), 4.83 (m, 1H), 3.59–3.29 (m, 12H); ¹³C NMR: δ 165.31, 145.40, 145.30, 141.12, 136.46, 127.42, 122.10, 59.25, 53.92, 42.09, 29.96.

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
Br1	0.40751 (2)	0.249349 (19)	0.929613 (9)	0.01727 (5)
Br2	−0.28556 (2)	0.41618 (2)	0.890082 (10)	0.01951 (5)
N3	0.12881 (16)	0.57574 (16)	0.91274 (7)	0.0122 (3)
O6	−0.07343 (15)	0.81594 (13)	1.03355 (7)	0.0166 (3)
O4	0.15459 (17)	0.56843 (14)	0.75554 (7)	0.0220 (3)
O1	0.19398 (19)	1.15503 (14)	0.77670 (7)	0.0252 (4)
N4	0.15130 (18)	0.73137 (16)	1.05021 (8)	0.0136 (3)
H15	0.2330	0.7141	1.0311	0.016*
O2	0.04981 (17)	1.19592 (14)	0.86354 (8)	0.0238 (3)
O5	0.14132 (18)	0.46394 (14)	1.10588 (8)	0.0254 (3)
H16	0.1682	0.4131	1.1369	0.038*
O3	0.35545 (18)	0.67865 (15)	0.74433 (8)	0.0262 (3)
C4	0.1362 (2)	0.98017 (19)	0.85101 (10)	0.0147 (4)
N2	0.23823 (19)	0.65829 (17)	0.77227 (8)	0.0167 (4)
C2	0.19306 (19)	0.7535 (2)	0.82703 (8)	0.0131 (3)
C7	0.23616 (19)	0.47445 (17)	0.89267 (10)	0.0124 (3)
H1	0.3231	0.5181	0.8763	0.015*
H2	0.1988	0.4190	0.8552	0.015*
C5	0.0816 (2)	0.94452 (18)	0.91548 (9)	0.0134 (4)
H3	0.0417	1.0093	0.9446	0.016*
C13	0.0571 (2)	0.5693 (2)	1.13547 (10)	0.0210 (4)
H4	0.0442	0.5532	1.1850	0.025*
H5	−0.0371	0.5708	1.1137	0.025*
C6	0.0866 (2)	0.81095 (18)	0.93645 (9)	0.0125 (3)
C8	0.2695 (2)	0.38799 (18)	0.95618 (10)	0.0162 (4)
H6	0.1819	0.3467	0.9734	0.019*
H7	0.3095	0.4432	0.9931	0.019*
C3	0.1980 (2)	0.88677 (18)	0.80689 (10)	0.0146 (4)
H8	0.2413	0.9125	0.7652	0.018*
C12	0.1305 (2)	0.7025 (2)	1.12466 (10)	0.0191 (4)
H9	0.0728	0.7730	1.1455	0.023*
H10	0.2232	0.7016	1.1479	0.023*
N1	0.12710 (19)	1.12055 (15)	0.82881 (9)	0.0179 (4)
C10	−0.0999 (2)	0.49488 (19)	0.86562 (10)	0.0174 (4)
H11	−0.0463	0.4330	0.8364	0.021*
H12	−0.1148	0.5771	0.8395	0.021*
C9	−0.0148 (2)	0.52491 (19)	0.93136 (10)	0.0138 (4)
H13	−0.0653	0.5913	0.9591	0.017*
H14	−0.0053	0.4439	0.9590	0.017*
C1	0.13690 (19)	0.70845 (17)	0.89094 (10)	0.0115 (3)
C11	0.0458 (2)	0.78393 (17)	1.01141 (9)	0.0129 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01734 (9)	0.01270 (9)	0.02178 (9)	0.00345 (8)	−0.00014 (7)	0.00288 (8)
Br2	0.01591 (9)	0.01879 (9)	0.02384 (10)	−0.00410 (8)	−0.00125 (8)	−0.00338 (8)
N3	0.0127 (7)	0.0088 (7)	0.0150 (7)	−0.0002 (6)	0.0005 (6)	0.0007 (6)
O6	0.0167 (7)	0.0160 (7)	0.0172 (7)	0.0020 (6)	0.0013 (6)	−0.0024 (5)
O4	0.0310 (8)	0.0170 (7)	0.0181 (7)	−0.0006 (6)	−0.0039 (6)	−0.0045 (6)
O1	0.0421 (10)	0.0152 (7)	0.0183 (7)	−0.0080 (7)	−0.0013 (7)	0.0037 (6)
N4	0.0161 (7)	0.0125 (8)	0.0122 (7)	0.0007 (7)	0.0013 (6)	0.0011 (6)
O2	0.0313 (9)	0.0097 (6)	0.0303 (8)	0.0025 (6)	−0.0018 (7)	0.0001 (6)
O5	0.0403 (9)	0.0167 (7)	0.0192 (7)	0.0052 (6)	0.0025 (8)	0.0051 (6)
O3	0.0331 (9)	0.0217 (8)	0.0236 (8)	0.0020 (7)	0.0135 (7)	−0.0008 (6)
C4	0.0165 (9)	0.0087 (9)	0.0187 (10)	−0.0017 (7)	−0.0046 (8)	0.0028 (7)
N2	0.0250 (10)	0.0143 (8)	0.0109 (8)	0.0047 (7)	0.0007 (7)	0.0032 (6)
C2	0.0146 (8)	0.0126 (8)	0.0122 (8)	0.0015 (8)	−0.0012 (6)	−0.0029 (8)
C7	0.0143 (9)	0.0087 (8)	0.0143 (8)	0.0010 (7)	0.0001 (8)	−0.0009 (7)
C5	0.0127 (8)	0.0114 (9)	0.0162 (9)	0.0011 (7)	−0.0015 (7)	−0.0022 (7)
C13	0.0254 (11)	0.0210 (10)	0.0166 (9)	0.0031 (9)	0.0037 (8)	0.0041 (8)
C6	0.0121 (8)	0.0122 (8)	0.0131 (9)	−0.0006 (7)	−0.0020 (8)	0.0000 (7)
C8	0.0201 (10)	0.0106 (9)	0.0178 (9)	0.0046 (7)	0.0007 (8)	0.0014 (7)
C3	0.0165 (9)	0.0148 (9)	0.0125 (8)	−0.0034 (7)	−0.0017 (7)	0.0024 (7)
C12	0.0263 (11)	0.0195 (9)	0.0117 (9)	0.0002 (8)	−0.0004 (8)	−0.0010 (7)
N1	0.0259 (10)	0.0103 (8)	0.0174 (8)	−0.0038 (6)	−0.0071 (7)	0.0015 (6)
C10	0.0141 (9)	0.0180 (10)	0.0201 (9)	−0.0044 (8)	0.0003 (8)	−0.0010 (7)
C9	0.0145 (9)	0.0103 (8)	0.0167 (9)	−0.0027 (7)	0.0003 (8)	0.0005 (7)
C1	0.0118 (8)	0.0105 (8)	0.0123 (8)	−0.0013 (6)	−0.0034 (8)	0.0008 (7)
C11	0.0179 (10)	0.0064 (9)	0.0142 (9)	−0.0033 (7)	0.0022 (7)	−0.0026 (6)

Geometric parameters (Å, º)

Br1—C8	1.9524 (19)	C7—C8	1.523 (3)
Br2—C10	1.953 (2)	C7—H1	0.9700
N3—C1	1.389 (2)	C7—H2	0.9700
N3—C7	1.470 (2)	C5—C6	1.391 (3)
N3—C9	1.471 (2)	C5—H3	0.9300
O6—C11	1.229 (2)	C13—C12	1.507 (3)
O4—N2	1.228 (2)	C13—H4	0.9700
O1—N1	1.225 (2)	C13—H5	0.9700
N4—C11	1.337 (2)	C6—C1	1.422 (3)
N4—C12	1.468 (2)	C6—C11	1.510 (3)
N4—H15	0.8600	C8—H6	0.9700
O2—N1	1.234 (2)	C8—H7	0.9700
O5—C13	1.427 (3)	C3—H8	0.9300
O5—H16	0.8200	C12—H9	0.9700
O3—N2	1.231 (2)	C12—H10	0.9700
C4—C5	1.382 (3)	C10—C9	1.517 (3)
C4—C3	1.382 (3)	C10—H11	0.9700
C4—N1	1.464 (2)	C10—H12	0.9700
N2—C2	1.475 (2)	C9—H13	0.9700
C2—C3	1.384 (3)	C9—H14	0.9700
C2—C1	1.405 (3)
C1—N3—C7	122.56 (15)	C7—C8—H6	109.9
C1—N3—C9	116.73 (15)	Br1—C8—H6	109.9
C7—N3—C9	116.27 (15)	C7—C8—H7	109.9
C11—N4—C12	121.34 (17)	Br1—C8—H7	109.9
C11—N4—H15	119.3	H6—C8—H7	108.3
C12—N4—H15	119.3	C4—C3—C2	117.52 (17)
C13—O5—H16	109.5	C4—C3—H8	121.2
C5—C4—C3	121.74 (17)	C2—C3—H8	121.2
C5—C4—N1	118.94 (17)	N4—C12—C13	111.46 (16)
C3—C4—N1	119.32 (17)	N4—C12—H9	109.3
O4—N2—O3	124.55 (17)	C13—C12—H9	109.3
O4—N2—C2	118.29 (16)	N4—C12—H10	109.3
O3—N2—C2	117.08 (17)	C13—C12—H10	109.3
C3—C2—C1	124.19 (17)	H9—C12—H10	108.0
C3—C2—N2	114.16 (16)	O1—N1—O2	124.33 (16)
C1—C2—N2	121.35 (17)	O1—N1—C4	118.37 (17)
N3—C7—C8	108.52 (15)	O2—N1—C4	117.28 (16)
N3—C7—H1	110.0	C9—C10—Br2	109.93 (13)
C8—C7—H1	110.0	C9—C10—H11	109.7
N3—C7—H2	110.0	Br2—C10—H11	109.7
C8—C7—H2	110.0	C9—C10—H12	109.7
H1—C7—H2	108.4	Br2—C10—H12	109.7
C4—C5—C6	119.45 (17)	H11—C10—H12	108.2
C4—C5—H3	120.3	N3—C9—C10	109.85 (15)
C6—C5—H3	120.3	N3—C9—H13	109.7
O5—C13—C12	110.20 (17)	C10—C9—H13	109.7
O5—C13—H4	109.6	N3—C9—H14	109.7
C12—C13—H4	109.6	C10—C9—H14	109.7
O5—C13—H5	109.6	H13—C9—H14	108.2
C12—C13—H5	109.6	N3—C1—C2	125.90 (16)
H4—C13—H5	108.1	N3—C1—C6	118.81 (16)
C5—C6—C1	121.43 (17)	C2—C1—C6	115.28 (16)
C5—C6—C11	115.90 (16)	O6—C11—N4	124.84 (17)
C1—C6—C11	122.54 (16)	O6—C11—C6	120.60 (17)
C7—C8—Br1	109.02 (13)	N4—C11—C6	114.45 (17)
O4—N2—C2—C3	−124.40 (19)	C1—N3—C9—C10	77.18 (19)
O3—N2—C2—C3	52.4 (2)	C7—N3—C9—C10	−79.83 (19)
O4—N2—C2—C1	49.6 (2)	Br2—C10—C9—N3	176.23 (12)
O3—N2—C2—C1	−133.55 (18)	C7—N3—C1—C2	32.4 (3)
C1—N3—C7—C8	138.33 (17)	C9—N3—C1—C2	−123.06 (19)
C9—N3—C7—C8	−66.1 (2)	C7—N3—C1—C6	−146.67 (17)
C3—C4—C5—C6	−1.0 (3)	C9—N3—C1—C6	57.9 (2)
N1—C4—C5—C6	178.55 (17)	C3—C2—C1—N3	179.36 (18)
C4—C5—C6—C1	−4.8 (3)	N2—C2—C1—N3	6.0 (3)
C4—C5—C6—C11	171.05 (17)	C3—C2—C1—C6	−1.6 (3)
N3—C7—C8—Br1	178.24 (12)	N2—C2—C1—C6	−174.94 (16)
C5—C4—C3—C2	5.1 (3)	C5—C6—C1—N3	−174.93 (17)
N1—C4—C3—C2	−174.38 (18)	C11—C6—C1—N3	9.5 (3)
C1—C2—C3—C4	−3.8 (3)	C5—C6—C1—C2	5.9 (3)
N2—C2—C3—C4	169.99 (17)	C11—C6—C1—C2	−169.69 (17)
C11—N4—C12—C13	82.7 (2)	C12—N4—C11—O6	2.2 (3)
O5—C13—C12—N4	59.7 (2)	C12—N4—C11—C6	178.33 (16)
C5—C4—N1—O1	169.40 (17)	C5—C6—C11—O6	58.7 (2)
C3—C4—N1—O1	−11.1 (3)	C1—C6—C11—O6	−125.44 (19)
C5—C4—N1—O2	−11.9 (3)	C5—C6—C11—N4	−117.59 (18)
C3—C4—N1—O2	167.65 (18)	C1—C6—C11—N4	58.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H15···O6^i	0.86	2.21	3.057 (2)	171
O5—H16···O3^ii	0.82	2.26	3.009 (2)	152

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