Crystal structure of rubidium methyl­diazo­tate

The title compound has been crystallized in liquid ammonia as a reaction product of the reductive ammonolysis of the natural compound streptozocin. Elemental rubidium was used as reduction agent as it is soluble in liquid ammonia, forming a blue solution. Reductive bond cleavage in biogenic materials under kinetically controlled conditions offers a new approach to gain access to sustainably produced raw materials.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](O-N) = 0.002 Å
• R factor = 0.017
• wR factor = 0.042
• Data-to-parameter ratio = 20.9

checkCIF/PLATON results

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Alert level C
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          3 Note
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       5.33 Ratio

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 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

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Computing details

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Rubidium methyldiazotate

Crystal data

Rb^+·CH3N2O^−	F(000) = 272
Mr = 144.52	Dx = 2.415 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8658 (1) Å	Cell parameters from 8481 reflections
b = 8.7614 (1) Å	θ = 3.1–32.1°
c = 7.2447 (1) Å	µ = 12.26 mm^−1
β = 114.219 (2)°	T = 123 K
V = 397.44 (1) Å^3	Block, colourless
Z = 4	0.29 × 0.17 × 0.15 mm

Data collection

Agilent SuperNova Dual Source diffractometer with an Eos detector	1210 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1068 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.051
Detector resolution: 15.9702 pixels mm^-1	θmax = 30.5°, θmin = 3.4°
phi and ω scans	h = −9→9
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012) based on expressions derived by Clark & Reid (1995)]	k = −12→12
Tmin = 0.267, Tmax = 0.267	l = −10→10
13443 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.017	All H-atom parameters refined
wR(F^2) = 0.042	w = 1/[σ^2(Fo^2) + (0.0256P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
1210 reflections	Δρmax = 0.56 e Å^−3
58 parameters	Δρmin = −0.86 e Å^−3

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Rb1	0.24027 (2)	0.64932 (2)	0.44893 (2)	0.01283 (6)
O1	0.6929 (2)	0.68315 (14)	0.5959 (2)	0.0159 (2)
N1	0.7933 (2)	0.67488 (17)	0.4770 (2)	0.0163 (3)
N2	0.8203 (2)	0.79640 (17)	0.3938 (2)	0.0159 (3)
C1	0.7331 (3)	0.9368 (2)	0.4396 (3)	0.0194 (3)
H2	0.583 (3)	0.928 (2)	0.408 (4)	0.027 (6)*
H3	0.753 (3)	1.018 (2)	0.352 (3)	0.016 (5)*
H1	0.812 (4)	0.967 (3)	0.587 (5)	0.049 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Rb1	0.01432 (9)	0.01265 (9)	0.01354 (9)	0.00103 (6)	0.00777 (6)	0.00118 (6)
O1	0.0194 (6)	0.0169 (6)	0.0160 (6)	−0.0005 (4)	0.0120 (5)	0.0004 (5)
N1	0.0190 (7)	0.0167 (8)	0.0158 (7)	0.0019 (5)	0.0098 (6)	0.0009 (6)
N2	0.0204 (7)	0.0145 (6)	0.0163 (7)	0.0029 (6)	0.0112 (6)	0.0019 (6)
C1	0.0294 (9)	0.0126 (8)	0.0223 (9)	0.0019 (7)	0.0167 (8)	0.0002 (7)

Geometric parameters (Å, º)

Rb1—Rb1^i	4.2210 (2)	N2—Rb1^v	3.0313 (14)
Rb1—Rb1^ii	4.2365 (3)	N2—Rb1^vi	3.0761 (15)
Rb1—Rb1^iii	5.2757 (2)	N2—C1	1.465 (2)
Rb1—C1^iv	3.7471 (18)	C1—Rb1^i	3.7471 (18)
O1—Rb1^i	2.8496 (12)	C1—Rb1^vi	3.6538 (18)
O1—Rb1^ii	2.9871 (12)	C1—Rb1^vii	3.7031 (19)
O1—N1	1.3074 (19)	C1—H2	0.97 (2)
N1—Rb1^v	3.1656 (15)	C1—H3	1.00 (2)
N1—Rb1^ii	2.9173 (15)	C1—H1	1.02 (3)
N1—N2	1.274 (2)
Rb1^ii—Rb1—Rb1^iii	113.582 (6)	Rb1^vii—C1—Rb1^i	90.16 (4)
Rb1^i—Rb1—Rb1^iii	85.861 (5)	Rb1^vi—C1—Rb1^i	156.42 (6)
Rb1^i—Rb1—Rb1^ii	77.186 (4)	Rb1^vi—C1—Rb1^vii	113.28 (5)
C1^iv—Rb1—Rb1^ii	73.60 (3)	Rb1^vii—C1—H2	94.8 (13)
C1^iv—Rb1—Rb1^iii	67.80 (3)	Rb1^i—C1—H2	78.4 (15)
C1^iv—Rb1—Rb1^i	127.36 (3)	Rb1^vi—C1—H2	101.1 (15)
Rb1^i—O1—Rb1^ii	129.33 (5)	Rb1^vi—C1—H3	58.0 (12)
N1—O1—Rb1^ii	74.24 (8)	Rb1^vii—C1—H3	55.4 (12)
N1—O1—Rb1^i	136.30 (10)	Rb1^i—C1—H3	144.9 (12)
Rb1^ii—N1—Rb1^v	95.44 (4)	Rb1^vii—C1—H1	63.8 (16)
O1—N1—Rb1^v	146.43 (12)	Rb1^i—C1—H1	39.6 (15)
O1—N1—Rb1^ii	80.21 (8)	Rb1^vi—C1—H1	149.8 (14)
N2—N1—Rb1^v	72.28 (9)	N2—C1—Rb1^vii	152.09 (11)
N2—N1—Rb1^ii	159.82 (11)	N2—C1—Rb1^i	102.26 (10)
N2—N1—O1	118.93 (13)	N2—C1—Rb1^vi	55.69 (8)
Rb1^v—N2—Rb1^vi	87.43 (4)	N2—C1—H2	112.1 (13)
N1—N2—Rb1^v	84.13 (10)	N2—C1—H3	106.3 (11)
N1—N2—Rb1^vi	128.81 (11)	N2—C1—H1	111.5 (16)
N1—N2—C1	116.27 (13)	H2—C1—H3	108.5 (17)
C1—N2—Rb1^v	141.49 (11)	H2—C1—H1	109 (2)
C1—N2—Rb1^vi	101.15 (10)	H3—C1—H1	109.3 (19)

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2; (iv) x−1/2, −y+3/2, z−1/2; (v) x+1, y, z; (vi) x+1/2, −y+3/2, z−1/2; (vii) −x+1, −y+2, −z+1.