Comparison of hydrogen bonds and diverse weak interactions of the nitro group in 2-methyl-4-nitroanilinium nitrate, bisulfate and two hexafluoridosilicates: elementary graph-set approach

Crystal structures of (H2m4na)NO₃ (1), (H2m4na)HSO₄ (2), (H2m4na)₂SiF₆ (3) and (H2m4na)₂SiF₆·2H₂O (4), where 2m4na = 2-methyl-4-nitroaniline, are presented. Two layers of interactions occur in the structures, N—H...O/F hydrogen bonds and interactions with the nitro group. Although diverse, hydrogen-bonding patterns are compared with each other by means of interrelations among elementary graph-set descriptors and descriptors of hydrogen-bonding patterns. Using mathematical relations, the gradual expansion of the ring patterns was shown in the crystal structures. Parallel and perpendicular arranged nitro groups form weak π(N)_NO2...π(O)_NO2 and π(N)_NO2...O_NO2 interactions, respectively. The π_NO2...π_ring interaction has an impact to the stabilization of parallel oriented nitro groups. Generally, weak interactions constructed by the nitro group occur in the studied crystals as follows: π(N)_NO2...π(O)_NO2, π_ring...π_ring, C—H...O (1); π(N)_NO2...π(O)_NO2, π(N)_NO2...O_NO2 (2); π(N)_NO2...π(O)_NO2, π(N)_NO2...O_NO2 (3); C—H...O (4).

Computing details

Data collection: CrysAlis 1.171.38.34a for M156, M2151, 1652; CrysAlis 1.171.33.42 for M155. For all compounds, cell refinement: CrysAlis 1.171.38.34a; data reduction: CrysAlis 1.171.38.34a; program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2014); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).

(M156)

Crystal data

C7H9N2O2·NO3	F(000) = 896
Mr = 215.17	Dx = 1.509 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9356 (4) Å	Cell parameters from 3268 reflections
b = 7.48389 (15) Å	θ = 2.4–25.4°
c = 17.1390 (4) Å	µ = 0.13 mm^−1
β = 112.052 (3)°	T = 295 K
V = 1894.48 (9) Å^3	Plate, brown
Z = 8	0.37 × 0.32 × 0.11 mm

Data collection

KUMA KM-4 with area CCD detector diffractometer	2785 reflections with I > 2σ(I)
ω–scan	Rint = 0.032
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 25.4°, θmin = 2.4°
Tmin = 0.873, Tmax = 1.000	h = −19→19
56168 measured reflections	k = −8→8
3268 independent reflections	l = −20→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	Only H-atom coordinates refined
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.5514P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = <0.001
3268 reflections	Δρmax = 0.16 e Å^−3
275 parameters	Δρmin = −0.18 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	Occ. (<1)
N1A	0.37336 (8)	0.95522 (17)	0.42470 (8)	0.0398 (3)
H1A1	0.4231	0.9200	0.4171	0.060*
H1A2	0.3718	0.9053	0.4713	0.060*
H1A3	0.3738	1.0736	0.4297	0.060*
C1A	0.29349 (10)	0.90065 (19)	0.35250 (9)	0.0348 (3)
C2A	0.20785 (10)	0.9414 (2)	0.35122 (10)	0.0394 (4)
C3A	0.13458 (11)	0.8897 (2)	0.27989 (11)	0.0490 (4)
H3A	0.0758	0.9131	0.2759	0.059*
C4A	0.14942 (12)	0.8038 (2)	0.21523 (10)	0.0508 (4)
N2A	0.07047 (14)	0.7571 (3)	0.13897 (12)	0.0766 (5)
O1A	−0.00372 (12)	0.8004 (3)	0.13528 (13)	0.1185 (7)
O2A	0.08473 (14)	0.6771 (3)	0.08302 (11)	0.1113 (7)
C5A	0.23451 (12)	0.7629 (2)	0.21755 (10)	0.0494 (4)
H5A	0.2423	0.7033	0.1731	0.059*
C6A	0.30766 (11)	0.8129 (2)	0.28766 (10)	0.0412 (4)
H6A	0.3662	0.7879	0.2914	0.049*
C7A	0.19334 (12)	1.0394 (3)	0.42176 (12)	0.0551 (5)
H7A1	0.1336	1.0900	0.4016	0.083*	0.5
H7A2	0.2374	1.1331	0.4419	0.083*	0.5
H7A3	0.1997	0.9576	0.4668	0.083*	0.5
H7A4	0.2469	1.0305	0.4720	0.083*	0.5
H7A5	0.1431	0.9874	0.4316	0.083*	0.5
H7A6	0.1808	1.1629	0.4067	0.083*	0.5
N1B	0.38892 (8)	0.46147 (18)	0.61102 (8)	0.0412 (3)
H1B1	0.3932	0.4186	0.5642	0.062*
H1B2	0.4375	0.4293	0.6553	0.062*
H1B3	0.3854	0.5801	0.6081	0.062*
C1B	0.30749 (10)	0.38959 (19)	0.62003 (9)	0.0349 (3)
C2B	0.22252 (10)	0.4310 (2)	0.56037 (9)	0.0386 (4)
C3B	0.14804 (11)	0.3626 (2)	0.57446 (10)	0.0450 (4)
H3B	0.0898	0.3852	0.5361	0.054*
C4B	0.16069 (11)	0.2620 (2)	0.64503 (11)	0.0452 (4)
N2B	0.08023 (12)	0.2023 (2)	0.66110 (12)	0.0643 (4)
O1B	0.00655 (10)	0.2516 (3)	0.61346 (13)	0.1026 (6)
O2B	0.09245 (12)	0.1064 (2)	0.72232 (12)	0.0891 (5)
C5B	0.24501 (11)	0.2192 (2)	0.70280 (11)	0.0462 (4)
H5B	0.2516	0.1491	0.7495	0.055*
C6B	0.31965 (11)	0.2836 (2)	0.68932 (10)	0.0404 (4)
H6B	0.3777	0.2557	0.7267	0.048*
C7B	0.20846 (12)	0.5475 (3)	0.48495 (11)	0.0529 (4)
H7B1	0.1486	0.5288	0.4438	0.079*	0.5
H7B2	0.2523	0.5175	0.4610	0.079*	0.5
H7B3	0.2155	0.6706	0.5019	0.079*	0.5
H7B4	0.2623	0.6158	0.4940	0.079*	0.5
H7B5	0.1586	0.6271	0.4768	0.079*	0.5
H7B6	0.1954	0.4740	0.4359	0.079*	0.5
N3A	0.43449 (8)	0.93022 (18)	0.64185 (8)	0.0400 (3)
O3A	0.46600 (9)	1.06503 (16)	0.62025 (9)	0.0595 (4)
O4A	0.37615 (8)	0.83862 (16)	0.58543 (7)	0.0533 (3)
O5A	0.45677 (9)	0.8842 (2)	0.71559 (7)	0.0640 (4)
N3B	0.41246 (8)	0.42160 (19)	0.42050 (8)	0.0412 (3)
O3B	0.37669 (10)	0.31629 (17)	0.45690 (9)	0.0627 (4)
O4B	0.41868 (9)	0.57972 (16)	0.44007 (8)	0.0626 (4)
O5B	0.43959 (10)	0.3602 (2)	0.36834 (8)	0.0751 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0396 (7)	0.0387 (7)	0.0405 (7)	−0.0024 (6)	0.0142 (6)	−0.0035 (6)
C1A	0.0390 (8)	0.0302 (7)	0.0341 (8)	−0.0025 (6)	0.0124 (6)	0.0046 (6)
C2A	0.0399 (8)	0.0357 (8)	0.0433 (9)	0.0002 (7)	0.0166 (7)	0.0071 (7)
C3A	0.0387 (9)	0.0516 (10)	0.0528 (10)	−0.0027 (7)	0.0125 (8)	0.0121 (8)
C4A	0.0513 (10)	0.0502 (10)	0.0387 (9)	−0.0126 (8)	0.0031 (8)	0.0073 (8)
N2A	0.0730 (13)	0.0831 (13)	0.0510 (11)	−0.0221 (10)	−0.0027 (9)	0.0070 (10)
O1A	0.0589 (11)	0.1549 (19)	0.1006 (14)	−0.0057 (11)	−0.0172 (10)	−0.0142 (13)
O2A	0.1175 (15)	0.1452 (18)	0.0486 (9)	−0.0439 (13)	0.0054 (9)	−0.0204 (11)
C5A	0.0654 (11)	0.0457 (9)	0.0352 (9)	−0.0063 (8)	0.0168 (8)	−0.0009 (7)
C6A	0.0469 (9)	0.0386 (8)	0.0404 (9)	0.0008 (7)	0.0192 (7)	0.0033 (7)
C7A	0.0528 (10)	0.0570 (11)	0.0632 (12)	0.0035 (8)	0.0306 (9)	−0.0033 (9)
N1B	0.0400 (7)	0.0431 (7)	0.0420 (7)	−0.0016 (6)	0.0171 (6)	0.0016 (6)
C1B	0.0385 (8)	0.0331 (7)	0.0352 (8)	−0.0023 (6)	0.0163 (6)	−0.0055 (6)
C2B	0.0409 (8)	0.0381 (8)	0.0362 (8)	0.0018 (7)	0.0136 (7)	−0.0039 (6)
C3B	0.0367 (8)	0.0504 (10)	0.0454 (9)	0.0007 (7)	0.0125 (7)	−0.0078 (8)
C4B	0.0432 (9)	0.0457 (9)	0.0534 (10)	−0.0063 (7)	0.0260 (8)	−0.0080 (8)
N2B	0.0571 (10)	0.0686 (11)	0.0796 (12)	−0.0092 (8)	0.0399 (9)	−0.0064 (9)
O1B	0.0459 (9)	0.1501 (18)	0.1164 (14)	−0.0025 (10)	0.0356 (9)	0.0233 (13)
O2B	0.0874 (11)	0.0959 (12)	0.1089 (13)	−0.0093 (9)	0.0652 (10)	0.0201 (11)
C5B	0.0550 (10)	0.0448 (9)	0.0449 (9)	−0.0020 (8)	0.0256 (8)	0.0033 (7)
C6B	0.0404 (8)	0.0426 (9)	0.0368 (8)	0.0023 (7)	0.0129 (7)	0.0010 (7)
C7B	0.0503 (10)	0.0585 (11)	0.0441 (10)	0.0047 (8)	0.0111 (8)	0.0095 (8)
N3A	0.0381 (7)	0.0430 (8)	0.0407 (8)	−0.0010 (6)	0.0167 (6)	−0.0045 (6)
O3A	0.0598 (8)	0.0469 (7)	0.0829 (9)	−0.0120 (6)	0.0395 (7)	−0.0071 (6)
O4A	0.0563 (7)	0.0482 (7)	0.0435 (7)	−0.0108 (6)	0.0053 (6)	−0.0013 (5)
O5A	0.0625 (8)	0.0915 (10)	0.0353 (7)	0.0028 (7)	0.0153 (6)	−0.0002 (6)
N3B	0.0392 (7)	0.0472 (8)	0.0334 (7)	−0.0034 (6)	0.0093 (6)	−0.0034 (6)
O3B	0.0862 (9)	0.0478 (7)	0.0749 (9)	−0.0217 (7)	0.0541 (8)	−0.0149 (6)
O4B	0.0696 (8)	0.0357 (7)	0.0663 (8)	0.0009 (6)	0.0072 (7)	0.0066 (6)
O5B	0.0733 (9)	0.1139 (12)	0.0493 (8)	−0.0205 (8)	0.0361 (7)	−0.0279 (8)

Geometric parameters (Å, º)

N1A—C1A	1.4613 (19)	N1B—H1B3	0.8900
N1A—H1A1	0.8900	C1B—C6B	1.380 (2)
N1A—H1A2	0.8900	C1B—C2B	1.391 (2)
N1A—H1A3	0.8900	C2B—C3B	1.394 (2)
C1A—C6A	1.380 (2)	C2B—C7B	1.505 (2)
C1A—C2A	1.391 (2)	C3B—C4B	1.374 (2)
C2A—C3A	1.391 (2)	C3B—H3B	0.9300
C2A—C7A	1.504 (2)	C4B—C5B	1.375 (2)
C3A—C4A	1.377 (3)	C4B—N2B	1.478 (2)
C3A—H3A	0.9300	N2B—O1B	1.209 (2)
C4A—C5A	1.376 (3)	N2B—O2B	1.225 (2)
C4A—N2A	1.476 (2)	C5B—C6B	1.381 (2)
N2A—O1A	1.205 (3)	C5B—H5B	0.9300
N2A—O2A	1.222 (3)	C6B—H6B	0.9300
C5A—C6A	1.375 (2)	C7B—H7B1	0.9600
C5A—H5A	0.9300	C7B—H7B2	0.9600
C6A—H6A	0.9300	C7B—H7B3	0.9600
C7A—H7A1	0.9600	C7B—H7B4	0.9600
C7A—H7A2	0.9600	C7B—H7B5	0.9600
C7A—H7A3	0.9600	C7B—H7B6	0.9600
C7A—H7A4	0.9600	N3A—O5A	1.2270 (17)
C7A—H7A5	0.9600	N3A—O3A	1.2436 (17)
C7A—H7A6	0.9600	N3A—O4A	1.2626 (17)
N1B—C1B	1.4655 (19)	N3B—O5B	1.2196 (18)
N1B—H1B1	0.8900	N3B—O4B	1.2238 (18)
N1B—H1B2	0.8900	N3B—O3B	1.2658 (18)
C1A—N1A—H1A1	109.5	C1B—N1B—H1B3	109.5
C1A—N1A—H1A2	109.5	H1B1—N1B—H1B3	109.5
H1A1—N1A—H1A2	109.5	H1B2—N1B—H1B3	109.5
C1A—N1A—H1A3	109.5	C6B—C1B—C2B	122.96 (14)
H1A1—N1A—H1A3	109.5	C6B—C1B—N1B	117.25 (13)
H1A2—N1A—H1A3	109.5	C2B—C1B—N1B	119.78 (13)
C6A—C1A—C2A	123.22 (14)	C1B—C2B—C3B	116.60 (14)
C6A—C1A—N1A	117.45 (13)	C1B—C2B—C7B	123.40 (14)
C2A—C1A—N1A	119.32 (13)	C3B—C2B—C7B	119.97 (14)
C1A—C2A—C3A	116.61 (15)	C4B—C3B—C2B	120.04 (15)
C1A—C2A—C7A	122.71 (14)	C4B—C3B—H3B	120.0
C3A—C2A—C7A	120.68 (15)	C2B—C3B—H3B	120.0
C4A—C3A—C2A	119.75 (16)	C3B—C4B—C5B	122.84 (15)
C4A—C3A—H3A	120.1	C3B—C4B—N2B	118.61 (16)
C2A—C3A—H3A	120.1	C5B—C4B—N2B	118.52 (16)
C5A—C4A—C3A	123.09 (15)	O1B—N2B—O2B	124.00 (17)
C5A—C4A—N2A	118.43 (18)	O1B—N2B—C4B	118.20 (18)
C3A—C4A—N2A	118.46 (18)	O2B—N2B—C4B	117.81 (18)
O1A—N2A—O2A	124.0 (2)	C4B—C5B—C6B	117.96 (15)
O1A—N2A—C4A	118.4 (2)	C4B—C5B—H5B	121.0
O2A—N2A—C4A	117.6 (2)	C6B—C5B—H5B	121.0
C6A—C5A—C4A	117.87 (16)	C1B—C6B—C5B	119.54 (15)
C6A—C5A—H5A	121.1	C1B—C6B—H6B	120.2
C4A—C5A—H5A	121.1	C5B—C6B—H6B	120.2
C5A—C6A—C1A	119.46 (15)	C2B—C7B—H7B1	109.5
C5A—C6A—H6A	120.3	C2B—C7B—H7B2	109.5
C1A—C6A—H6A	120.3	H7B1—C7B—H7B2	109.5
C2A—C7A—H7A1	109.5	C2B—C7B—H7B3	109.5
C2A—C7A—H7A2	109.5	H7B1—C7B—H7B3	109.5
H7A1—C7A—H7A2	109.5	H7B2—C7B—H7B3	109.5
C2A—C7A—H7A3	109.5	C2B—C7B—H7B4	109.5
H7A1—C7A—H7A3	109.5	H7B1—C7B—H7B4	141.1
H7A2—C7A—H7A3	109.5	H7B2—C7B—H7B4	56.3
C2A—C7A—H7A4	109.5	H7B3—C7B—H7B4	56.3
H7A1—C7A—H7A4	141.1	C2B—C7B—H7B5	109.5
H7A2—C7A—H7A4	56.3	H7B1—C7B—H7B5	56.3
H7A3—C7A—H7A4	56.3	H7B2—C7B—H7B5	141.1
C2A—C7A—H7A5	109.5	H7B3—C7B—H7B5	56.3
H7A1—C7A—H7A5	56.3	H7B4—C7B—H7B5	109.5
H7A2—C7A—H7A5	141.1	C2B—C7B—H7B6	109.5
H7A3—C7A—H7A5	56.3	H7B1—C7B—H7B6	56.3
H7A4—C7A—H7A5	109.5	H7B2—C7B—H7B6	56.3
C2A—C7A—H7A6	109.5	H7B3—C7B—H7B6	141.1
H7A1—C7A—H7A6	56.3	H7B4—C7B—H7B6	109.5
H7A2—C7A—H7A6	56.3	H7B5—C7B—H7B6	109.5
H7A3—C7A—H7A6	141.1	O5A—N3A—O3A	122.79 (14)
H7A4—C7A—H7A6	109.5	O5A—N3A—O4A	118.78 (14)
H7A5—C7A—H7A6	109.5	O3A—N3A—O4A	118.42 (13)
C1B—N1B—H1B1	109.5	O5B—N3B—O4B	123.39 (15)
C1B—N1B—H1B2	109.5	O5B—N3B—O3B	118.43 (14)
H1B1—N1B—H1B2	109.5	O4B—N3B—O3B	118.17 (14)
C6A—C1A—C2A—C3A	−0.3 (2)	C6B—C1B—C2B—C3B	1.3 (2)
N1A—C1A—C2A—C3A	178.49 (13)	N1B—C1B—C2B—C3B	−178.00 (13)
C6A—C1A—C2A—C7A	−179.11 (15)	C6B—C1B—C2B—C7B	179.53 (15)
N1A—C1A—C2A—C7A	−0.3 (2)	N1B—C1B—C2B—C7B	0.2 (2)
C1A—C2A—C3A—C4A	−0.3 (2)	C1B—C2B—C3B—C4B	0.8 (2)
C7A—C2A—C3A—C4A	178.52 (15)	C7B—C2B—C3B—C4B	−177.46 (15)
C2A—C3A—C4A—C5A	0.9 (3)	C2B—C3B—C4B—C5B	−2.1 (3)
C2A—C3A—C4A—N2A	−177.58 (15)	C2B—C3B—C4B—N2B	175.74 (15)
C5A—C4A—N2A—O1A	−176.5 (2)	C3B—C4B—N2B—O1B	−3.4 (3)
C3A—C4A—N2A—O1A	2.0 (3)	C5B—C4B—N2B—O1B	174.51 (19)
C5A—C4A—N2A—O2A	3.1 (3)	C3B—C4B—N2B—O2B	176.98 (17)
C3A—C4A—N2A—O2A	−178.32 (19)	C5B—C4B—N2B—O2B	−5.1 (3)
C3A—C4A—C5A—C6A	−0.8 (3)	C3B—C4B—C5B—C6B	1.1 (3)
N2A—C4A—C5A—C6A	177.66 (15)	N2B—C4B—C5B—C6B	−176.69 (15)
C4A—C5A—C6A—C1A	0.2 (2)	C2B—C1B—C6B—C5B	−2.3 (2)
C2A—C1A—C6A—C5A	0.3 (2)	N1B—C1B—C6B—C5B	177.06 (14)
N1A—C1A—C6A—C5A	−178.45 (14)	C4B—C5B—C6B—C1B	1.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A1···O3A^i	0.89	2.10	2.9412 (17)	158
N1A—H1A2···O4A	0.89	2.00	2.8741 (17)	169
N1A—H1A3···N3B^ii	0.89	2.69	3.5509 (19)	162
N1A—H1A3···O3B^ii	0.89	1.87	2.7545 (18)	171
C6A—H6A···O5A^iii	0.93	2.61	3.399 (2)	142
N1B—H1B1···N3B	0.89	2.59	3.4367 (18)	158
N1B—H1B1···O3B	0.89	1.92	2.7944 (18)	168
N1B—H1B1···O4B	0.89	2.61	3.2612 (19)	131
N1B—H1B2···O5A^iv	0.89	2.25	3.1186 (18)	166
N1B—H1B3···O4A	0.89	1.97	2.8519 (18)	172
C6B—H6B···O5A^iv	0.93	2.63	3.400 (2)	141
C6B—H6B···O5B^v	0.93	2.41	3.134 (2)	134

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

(M155)

Crystal data

C7H9N2O2·HO4S	F(000) = 520
Mr = 250.23	Dx = 1.639 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9394 (4) Å	Cell parameters from 1970 reflections
b = 5.01801 (11) Å	θ = 2.6–26.7°
c = 12.9310 (3) Å	µ = 0.34 mm^−1
β = 101.367 (2)°	T = 295 K
V = 1013.99 (4) Å^3	Plate, brown
Z = 4	0.36 × 0.34 × 0.06 mm

Data collection

KUMA KM-4 with area CCD detector diffractometer	1814 reflections with I > 2σ(I)
ω–scan	Rint = 0.017
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 26.7°, θmin = 2.6°
Tmin = 0.894, Tmax = 1.000	h = −19→19
8813 measured reflections	k = −6→5
1970 independent reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.077	w = 1/[σ^2(Fo^2) + (0.0381P)^2 + 0.4906P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = <0.001
1970 reflections	Δρmax = 0.27 e Å^−3
151 parameters	Δρmin = −0.49 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
S1	0.06794 (2)	0.49901 (7)	0.15921 (3)	0.01989 (13)
O3	0.13034 (7)	0.4330 (3)	0.25257 (9)	0.0330 (3)
O4	0.06022 (8)	0.8094 (2)	0.15316 (9)	0.0323 (3)
H4A	0.0459 (16)	0.863 (5)	0.206 (2)	0.062 (8)*
O5	−0.01632 (7)	0.3965 (2)	0.16409 (8)	0.0305 (3)
O6	0.09488 (7)	0.4334 (2)	0.06186 (8)	0.0267 (3)
C1	0.23391 (10)	0.5726 (3)	0.51408 (11)	0.0231 (3)
N1	0.14196 (8)	0.5558 (3)	0.46950 (10)	0.0249 (3)
H1A	0.1186	0.4278	0.5022	0.037*
H1B	0.1343	0.5185	0.4010	0.037*
H1C	0.1172	0.7110	0.4783	0.037*
C2	0.28394 (10)	0.7502 (3)	0.46987 (12)	0.0263 (3)
C3	0.37091 (10)	0.7522 (3)	0.51214 (12)	0.0296 (4)
H3	0.4067	0.8697	0.4859	0.036*
C4	0.40429 (10)	0.5808 (3)	0.59284 (12)	0.0282 (3)
N2	0.49761 (9)	0.5778 (3)	0.63155 (11)	0.0343 (3)
O1	0.54059 (8)	0.7464 (3)	0.59825 (12)	0.0514 (4)
O2	0.52842 (8)	0.4055 (3)	0.69338 (12)	0.0499 (4)
C5	0.35434 (11)	0.4082 (4)	0.63746 (13)	0.0337 (4)
H5	0.3784	0.2960	0.6926	0.040*
C6	0.26746 (11)	0.4075 (4)	0.59757 (13)	0.0317 (4)
H6	0.2316	0.2964	0.6267	0.038*
C7	0.24754 (12)	0.9305 (4)	0.37924 (15)	0.0398 (4)
H7A	0.1929	0.9965	0.3882	0.060*
H7B	0.2408	0.8327	0.3143	0.060*
H7C	0.2857	1.0776	0.3773	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0235 (2)	0.0198 (2)	0.0169 (2)	0.00053 (14)	0.00529 (15)	0.00030 (13)
O3	0.0331 (7)	0.0412 (7)	0.0223 (6)	0.0060 (5)	−0.0006 (5)	0.0009 (5)
O4	0.0504 (8)	0.0205 (6)	0.0307 (6)	0.0018 (5)	0.0194 (6)	−0.0002 (5)
O5	0.0291 (6)	0.0390 (7)	0.0247 (6)	−0.0089 (5)	0.0083 (5)	0.0009 (5)
O6	0.0320 (6)	0.0288 (6)	0.0210 (5)	0.0041 (5)	0.0097 (4)	−0.0015 (4)
C1	0.0228 (8)	0.0260 (8)	0.0206 (7)	−0.0013 (6)	0.0041 (6)	−0.0026 (6)
N1	0.0244 (7)	0.0291 (7)	0.0213 (6)	0.0010 (5)	0.0049 (5)	0.0019 (5)
C2	0.0317 (8)	0.0245 (8)	0.0232 (7)	−0.0006 (6)	0.0063 (6)	0.0013 (6)
C3	0.0298 (9)	0.0305 (8)	0.0295 (8)	−0.0061 (7)	0.0080 (7)	0.0025 (7)
C4	0.0236 (8)	0.0337 (9)	0.0265 (8)	−0.0029 (7)	0.0030 (6)	−0.0023 (7)
N2	0.0269 (7)	0.0418 (8)	0.0335 (8)	−0.0035 (6)	0.0046 (6)	−0.0016 (7)
O1	0.0313 (7)	0.0636 (10)	0.0588 (9)	−0.0153 (7)	0.0074 (6)	0.0121 (7)
O2	0.0325 (7)	0.0577 (9)	0.0553 (8)	0.0046 (6)	−0.0020 (6)	0.0174 (7)
C5	0.0303 (9)	0.0392 (10)	0.0289 (8)	−0.0026 (7)	−0.0005 (7)	0.0107 (7)
C6	0.0290 (9)	0.0373 (9)	0.0281 (8)	−0.0065 (7)	0.0042 (7)	0.0090 (7)
C7	0.0395 (10)	0.0389 (10)	0.0382 (10)	−0.0059 (8)	0.0010 (8)	0.0145 (8)

Geometric parameters (Å, º)

S1—O3	1.4434 (11)	C3—C4	1.376 (2)
S1—O6	1.4458 (10)	C3—H3	0.9300
S1—O5	1.4511 (11)	C4—C5	1.378 (2)
S1—O4	1.5631 (12)	C4—N2	1.473 (2)
O4—H4A	0.80 (3)	N2—O2	1.214 (2)
C1—C6	1.382 (2)	N2—O1	1.220 (2)
C1—C2	1.391 (2)	C5—C6	1.379 (2)
C1—N1	1.4679 (19)	C5—H5	0.9300
N1—H1A	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C7—H7A	0.9600
N1—H1C	0.8900	C7—H7B	0.9600
C2—C3	1.386 (2)	C7—H7C	0.9600
C2—C7	1.504 (2)
O3—S1—O6	113.70 (7)	C4—C3—H3	120.0
O3—S1—O5	111.92 (7)	C2—C3—H3	120.0
O6—S1—O5	113.16 (7)	C3—C4—C5	122.79 (15)
O3—S1—O4	107.76 (7)	C3—C4—N2	118.55 (14)
O6—S1—O4	102.55 (6)	C5—C4—N2	118.65 (15)
O5—S1—O4	106.92 (7)	O2—N2—O1	122.99 (15)
S1—O4—H4A	109.0 (18)	O2—N2—C4	118.79 (15)
C6—C1—C2	122.67 (15)	O1—N2—C4	118.21 (15)
C6—C1—N1	118.37 (14)	C4—C5—C6	117.75 (16)
C2—C1—N1	118.95 (14)	C4—C5—H5	121.1
C1—N1—H1A	109.5	C6—C5—H5	121.1
C1—N1—H1B	109.5	C5—C6—C1	119.74 (15)
H1A—N1—H1B	109.5	C5—C6—H6	120.1
C1—N1—H1C	109.5	C1—C6—H6	120.1
H1A—N1—H1C	109.5	C2—C7—H7A	109.5
H1B—N1—H1C	109.5	C2—C7—H7B	109.5
C3—C2—C1	116.89 (14)	H7A—C7—H7B	109.5
C3—C2—C7	120.32 (14)	C2—C7—H7C	109.5
C1—C2—C7	122.77 (15)	H7A—C7—H7C	109.5
C4—C3—C2	120.10 (15)	H7B—C7—H7C	109.5
C6—C1—C2—C3	1.2 (2)	C5—C4—N2—O2	7.6 (2)
N1—C1—C2—C3	−177.76 (13)	C3—C4—N2—O1	7.6 (2)
C6—C1—C2—C7	−179.81 (16)	C5—C4—N2—O1	−173.75 (17)
N1—C1—C2—C7	1.2 (2)	C3—C4—C5—C6	0.9 (3)
C1—C2—C3—C4	1.0 (2)	N2—C4—C5—C6	−177.75 (16)
C7—C2—C3—C4	−177.94 (16)	C4—C5—C6—C1	1.4 (3)
C2—C3—C4—C5	−2.1 (3)	C2—C1—C6—C5	−2.5 (3)
C2—C3—C4—N2	176.49 (14)	N1—C1—C6—C5	176.50 (15)
C3—C4—N2—O2	−171.08 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O5^i	0.80 (3)	1.84 (3)	2.6301 (15)	165 (3)
N1—H1A···O6^ii	0.89	2.03	2.8929 (17)	162
N1—H1B···O3	0.89	1.96	2.8423 (17)	174
N1—H1C···O5^i	0.89	2.38	2.9246 (17)	120
N1—H1C···O6^iii	0.89	2.15	2.9853 (17)	156
C3—H3···O1^iv	0.93	2.44	3.339 (2)	162
C6—H6···O6^ii	0.93	2.46	3.195 (2)	136

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

(M2151)

Crystal data

2(C7H9N2O2)·F6Si	F(000) = 920
Mr = 448.41	Dx = 1.588 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.1643 (3) Å	Cell parameters from 4034 reflections
b = 10.2128 (4) Å	θ = 2.1–26.9°
c = 29.8240 (16) Å	µ = 0.21 mm^−1
β = 92.439 (4)°	T = 295 K
V = 1875.85 (16) Å^3	Plate, yellow
Z = 4	0.79 × 0.45 × 0.02 mm

Data collection

KUMA KM-4 with area CCD detector diffractometer	2877 reflections with I > 2σ(I)
ω–scan	Rint = 0.040
Absorption correction: gaussian CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 26.9°, θmin = 2.1°
Tmin = 0.906, Tmax = 0.997	h = −7→7
24281 measured reflections	k = −12→13
4034 independent reflections	l = −37→37

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	Only H-atom coordinates refined
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0566P)^2 + 0.9712P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = <0.001
4034 reflections	Δρmax = 0.35 e Å^−3
269 parameters	Δρmin = −0.29 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
Si1A	0.5000	1.0000	0.0000	0.0309 (2)
F1A	0.6859 (2)	1.09680 (14)	0.02530 (5)	0.0529 (4)
F2A	0.4057 (2)	0.96016 (15)	0.05019 (4)	0.0519 (4)
F3A	0.6738 (2)	0.87212 (14)	0.00348 (5)	0.0600 (4)
Si1B	0.0000	0.5000	0.0000	0.0318 (2)
F1B	−0.0409 (3)	0.36342 (14)	0.02863 (6)	0.0666 (5)
F2B	0.2081 (3)	0.42663 (15)	−0.02408 (5)	0.0652 (5)
F3B	0.1695 (3)	0.55403 (17)	0.04110 (6)	0.0847 (6)
C1A	0.9953 (3)	0.8479 (2)	0.10697 (7)	0.0349 (5)
N1A	1.0368 (3)	0.81848 (19)	0.05964 (6)	0.0408 (4)
H1A1	0.9240	0.8445	0.0423	0.061*
H1A2	1.0558	0.7327	0.0564	0.061*
H1A3	1.1557	0.8606	0.0517	0.061*
C2A	1.1240 (4)	0.7907 (2)	0.14093 (7)	0.0389 (5)
C3A	1.0796 (4)	0.8239 (2)	0.18484 (7)	0.0406 (5)
H3A	1.1593	0.7861	0.2087	0.049*
C4A	0.9181 (4)	0.9126 (2)	0.19305 (7)	0.0385 (5)
N2A	0.8829 (3)	0.9517 (2)	0.23979 (7)	0.0475 (5)
O1A	0.9724 (3)	0.8876 (2)	0.26990 (6)	0.0578 (5)
O2A	0.7681 (3)	1.0461 (2)	0.24623 (7)	0.0716 (6)
C5A	0.7916 (4)	0.9686 (3)	0.15919 (8)	0.0497 (6)
H5A	0.6819	1.0275	0.1655	0.060*
C6A	0.8326 (4)	0.9347 (2)	0.11562 (8)	0.0478 (6)
H6A	0.7495	0.9709	0.0920	0.057*
C7A	1.3064 (5)	0.6981 (3)	0.13207 (9)	0.0682 (8)
H7A1	1.2480	0.6176	0.1201	0.102*
H7A2	1.3876	0.6807	0.1596	0.102*
H7A3	1.4001	0.7367	0.1108	0.102*
N1B	0.5134 (3)	0.34784 (18)	0.05360 (6)	0.0413 (4)
H1B1	0.4205	0.4100	0.0445	0.062*
H1B2	0.4936	0.2770	0.0365	0.062*
H1B3	0.6487	0.3768	0.0514	0.062*
C1B	0.4761 (3)	0.3143 (2)	0.10070 (7)	0.0351 (5)
C2B	0.5978 (4)	0.3735 (2)	0.13517 (7)	0.0380 (5)
C3B	0.5565 (4)	0.3347 (2)	0.17880 (7)	0.0400 (5)
H3B	0.6315	0.3734	0.2031	0.048*
C4B	0.4045 (3)	0.2392 (2)	0.18591 (7)	0.0371 (5)
N2B	0.3732 (3)	0.1952 (2)	0.23243 (7)	0.0465 (5)
O1B	0.4557 (3)	0.25986 (19)	0.26303 (5)	0.0528 (4)
O2B	0.2690 (3)	0.0962 (2)	0.23778 (7)	0.0745 (6)
C5B	0.2831 (4)	0.1819 (2)	0.15133 (8)	0.0465 (6)
H5B	0.1796	0.1185	0.1570	0.056*
C6B	0.3194 (4)	0.2213 (2)	0.10815 (8)	0.0442 (5)
H6B	0.2386	0.1855	0.0841	0.053*
C7B	0.7692 (5)	0.4754 (3)	0.12784 (9)	0.0598 (7)
H7B1	0.8921	0.4350	0.1148	0.090*
H7B2	0.8136	0.5141	0.1561	0.090*
H7B3	0.7112	0.5419	0.1080	0.090*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1A	0.0311 (4)	0.0315 (4)	0.0300 (4)	−0.0014 (3)	−0.0012 (3)	0.0005 (3)
F1A	0.0536 (8)	0.0572 (8)	0.0469 (8)	−0.0194 (7)	−0.0102 (6)	−0.0016 (7)
F2A	0.0517 (8)	0.0703 (9)	0.0339 (7)	−0.0141 (7)	0.0028 (6)	0.0058 (6)
F3A	0.0651 (9)	0.0558 (9)	0.0579 (9)	0.0264 (7)	−0.0101 (7)	−0.0063 (7)
Si1B	0.0363 (4)	0.0282 (4)	0.0312 (4)	−0.0015 (3)	0.0025 (3)	−0.0009 (3)
F1B	0.0843 (11)	0.0439 (8)	0.0739 (11)	0.0074 (8)	0.0286 (9)	0.0221 (7)
F2B	0.0688 (10)	0.0559 (9)	0.0733 (11)	0.0188 (8)	0.0321 (8)	0.0060 (8)
F3B	0.0956 (13)	0.0616 (10)	0.0921 (13)	0.0131 (9)	−0.0518 (11)	−0.0289 (10)
C1A	0.0366 (11)	0.0377 (11)	0.0303 (11)	−0.0062 (9)	−0.0008 (9)	−0.0018 (9)
N1A	0.0450 (11)	0.0445 (11)	0.0325 (10)	−0.0051 (8)	−0.0016 (8)	−0.0035 (8)
C2A	0.0406 (12)	0.0385 (12)	0.0370 (12)	0.0032 (9)	−0.0045 (9)	−0.0039 (10)
C3A	0.0452 (13)	0.0422 (12)	0.0334 (12)	0.0034 (10)	−0.0069 (9)	0.0020 (10)
C4A	0.0372 (12)	0.0459 (12)	0.0326 (11)	−0.0042 (10)	0.0022 (9)	−0.0029 (10)
N2A	0.0407 (11)	0.0641 (14)	0.0377 (11)	−0.0061 (10)	0.0030 (9)	−0.0061 (10)
O1A	0.0512 (10)	0.0868 (14)	0.0353 (9)	−0.0074 (10)	−0.0006 (8)	0.0033 (9)
O2A	0.0703 (13)	0.0864 (15)	0.0583 (12)	0.0219 (11)	0.0045 (10)	−0.0235 (11)
C5A	0.0427 (13)	0.0616 (16)	0.0442 (14)	0.0158 (11)	−0.0038 (11)	−0.0033 (12)
C6A	0.0481 (14)	0.0570 (15)	0.0371 (13)	0.0101 (11)	−0.0101 (10)	0.0006 (11)
C7A	0.0741 (19)	0.078 (2)	0.0514 (16)	0.0353 (16)	−0.0146 (14)	−0.0168 (15)
N1B	0.0501 (11)	0.0422 (10)	0.0316 (10)	0.0021 (9)	0.0032 (8)	0.0009 (8)
C1B	0.0376 (11)	0.0365 (11)	0.0315 (11)	0.0070 (9)	0.0043 (9)	0.0028 (9)
C2B	0.0377 (12)	0.0400 (12)	0.0362 (12)	−0.0016 (9)	0.0016 (9)	0.0001 (9)
C3B	0.0399 (12)	0.0466 (13)	0.0333 (12)	−0.0030 (10)	−0.0003 (9)	−0.0039 (10)
C4B	0.0361 (11)	0.0434 (12)	0.0321 (11)	0.0010 (9)	0.0040 (9)	0.0015 (9)
N2B	0.0428 (11)	0.0575 (13)	0.0395 (11)	0.0002 (10)	0.0050 (9)	0.0057 (10)
O1B	0.0516 (10)	0.0731 (12)	0.0333 (9)	0.0028 (9)	−0.0013 (7)	−0.0019 (8)
O2B	0.0834 (15)	0.0844 (15)	0.0556 (12)	−0.0376 (12)	0.0035 (10)	0.0193 (11)
C5B	0.0480 (14)	0.0505 (14)	0.0413 (13)	−0.0139 (11)	0.0048 (10)	−0.0011 (11)
C6B	0.0482 (13)	0.0492 (13)	0.0350 (12)	−0.0069 (11)	−0.0014 (10)	−0.0063 (10)
C7B	0.0647 (17)	0.0689 (18)	0.0460 (15)	−0.0249 (14)	0.0037 (13)	0.0053 (13)

Geometric parameters (Å, º)

Si1A—F1A	1.6694 (12)	C5A—C6A	1.378 (3)
Si1A—F1A^i	1.6694 (12)	C5A—H5A	0.9300
Si1A—F2A^i	1.6786 (13)	C6A—H6A	0.9300
Si1A—F2A	1.6787 (12)	C7A—H7A1	0.9600
Si1A—F3A	1.6894 (13)	C7A—H7A2	0.9600
Si1A—F3A^i	1.6895 (13)	C7A—H7A3	0.9600
Si1B—F1B^ii	1.6603 (14)	N1B—C1B	1.473 (3)
Si1B—F1B	1.6603 (14)	N1B—H1B1	0.8900
Si1B—F3B	1.6701 (15)	N1B—H1B2	0.8900
Si1B—F3B^ii	1.6702 (15)	N1B—H1B3	0.8900
Si1B—F2B	1.6739 (13)	C1B—C6B	1.379 (3)
Si1B—F2B^ii	1.6739 (13)	C1B—C2B	1.386 (3)
C1A—C6A	1.372 (3)	C2B—C3B	1.394 (3)
C1A—C2A	1.389 (3)	C2B—C7B	1.505 (3)
C1A—N1A	1.476 (3)	C3B—C4B	1.376 (3)
N1A—H1A1	0.8900	C3B—H3B	0.9300
N1A—H1A2	0.8900	C4B—C5B	1.378 (3)
N1A—H1A3	0.8900	C4B—N2B	1.478 (3)
C2A—C3A	1.391 (3)	N2B—O2B	1.212 (3)
C2A—C7A	1.501 (3)	N2B—O1B	1.220 (3)
C3A—C4A	1.376 (3)	C5B—C6B	1.376 (3)
C3A—H3A	0.9300	C5B—H5B	0.9300
C4A—C5A	1.374 (3)	C6B—H6B	0.9300
C4A—N2A	1.475 (3)	C7B—H7B1	0.9600
N2A—O2A	1.215 (3)	C7B—H7B2	0.9600
N2A—O1A	1.224 (3)	C7B—H7B3	0.9600
F1A—Si1A—F1A^i	180.0	O2A—N2A—O1A	123.8 (2)
F1A—Si1A—F2A^i	90.14 (7)	O2A—N2A—C4A	118.3 (2)
F1A^i—Si1A—F2A^i	89.86 (7)	O1A—N2A—C4A	117.9 (2)
F1A—Si1A—F2A	89.86 (7)	C4A—C5A—C6A	117.9 (2)
F1A^i—Si1A—F2A	90.14 (7)	C4A—C5A—H5A	121.1
F2A^i—Si1A—F2A	180.0	C6A—C5A—H5A	121.1
F1A—Si1A—F3A	90.50 (7)	C1A—C6A—C5A	120.3 (2)
F1A^i—Si1A—F3A	89.50 (7)	C1A—C6A—H6A	119.9
F2A^i—Si1A—F3A	89.97 (8)	C5A—C6A—H6A	119.9
F2A—Si1A—F3A	90.03 (8)	C2A—C7A—H7A1	109.5
F1A—Si1A—F3A^i	89.50 (7)	C2A—C7A—H7A2	109.5
F1A^i—Si1A—F3A^i	90.50 (7)	H7A1—C7A—H7A2	109.5
F2A^i—Si1A—F3A^i	90.03 (8)	C2A—C7A—H7A3	109.5
F2A—Si1A—F3A^i	89.97 (8)	H7A1—C7A—H7A3	109.5
F3A—Si1A—F3A^i	180.0	H7A2—C7A—H7A3	109.5
F1B^ii—Si1B—F1B	180.0	C1B—N1B—H1B1	109.5
F1B^ii—Si1B—F3B	89.76 (10)	C1B—N1B—H1B2	109.5
F1B—Si1B—F3B	90.23 (10)	H1B1—N1B—H1B2	109.5
F1B^ii—Si1B—F3B^ii	90.23 (10)	C1B—N1B—H1B3	109.5
F1B—Si1B—F3B^ii	89.77 (10)	H1B1—N1B—H1B3	109.5
F3B—Si1B—F3B^ii	180.0	H1B2—N1B—H1B3	109.5
F1B^ii—Si1B—F2B	91.11 (7)	C6B—C1B—C2B	122.8 (2)
F1B—Si1B—F2B	88.89 (7)	C6B—C1B—N1B	116.91 (19)
F3B—Si1B—F2B	89.77 (9)	C2B—C1B—N1B	120.27 (19)
F3B^ii—Si1B—F2B	90.23 (9)	C1B—C2B—C3B	117.0 (2)
F1B^ii—Si1B—F2B^ii	88.89 (7)	C1B—C2B—C7B	123.7 (2)
F1B—Si1B—F2B^ii	91.11 (7)	C3B—C2B—C7B	119.3 (2)
F3B—Si1B—F2B^ii	90.23 (9)	C4B—C3B—C2B	119.9 (2)
F3B^ii—Si1B—F2B^ii	89.78 (9)	C4B—C3B—H3B	120.1
F2B—Si1B—F2B^ii	180.0	C2B—C3B—H3B	120.1
C6A—C1A—C2A	122.3 (2)	C3B—C4B—C5B	122.5 (2)
C6A—C1A—N1A	118.00 (19)	C3B—C4B—N2B	118.5 (2)
C2A—C1A—N1A	119.66 (19)	C5B—C4B—N2B	119.0 (2)
C1A—N1A—H1A1	109.5	O2B—N2B—O1B	124.0 (2)
C1A—N1A—H1A2	109.5	O2B—N2B—C4B	117.9 (2)
H1A1—N1A—H1A2	109.5	O1B—N2B—C4B	118.1 (2)
C1A—N1A—H1A3	109.5	C6B—C5B—C4B	118.1 (2)
H1A1—N1A—H1A3	109.5	C6B—C5B—H5B	120.9
H1A2—N1A—H1A3	109.5	C4B—C5B—H5B	120.9
C1A—C2A—C3A	117.1 (2)	C5B—C6B—C1B	119.6 (2)
C1A—C2A—C7A	123.1 (2)	C5B—C6B—H6B	120.2
C3A—C2A—C7A	119.9 (2)	C1B—C6B—H6B	120.2
C4A—C3A—C2A	120.0 (2)	C2B—C7B—H7B1	109.5
C4A—C3A—H3A	120.0	C2B—C7B—H7B2	109.5
C2A—C3A—H3A	120.0	H7B1—C7B—H7B2	109.5
C5A—C4A—C3A	122.4 (2)	C2B—C7B—H7B3	109.5
C5A—C4A—N2A	118.7 (2)	H7B1—C7B—H7B3	109.5
C3A—C4A—N2A	118.9 (2)	H7B2—C7B—H7B3	109.5
C6A—C1A—C2A—C3A	0.8 (3)	C6B—C1B—C2B—C3B	0.3 (3)
N1A—C1A—C2A—C3A	178.89 (19)	N1B—C1B—C2B—C3B	−178.68 (19)
C6A—C1A—C2A—C7A	−178.4 (2)	C6B—C1B—C2B—C7B	−179.8 (2)
N1A—C1A—C2A—C7A	−0.3 (3)	N1B—C1B—C2B—C7B	1.2 (3)
C1A—C2A—C3A—C4A	−1.7 (3)	C1B—C2B—C3B—C4B	1.7 (3)
C7A—C2A—C3A—C4A	177.5 (2)	C7B—C2B—C3B—C4B	−178.2 (2)
C2A—C3A—C4A—C5A	1.8 (4)	C2B—C3B—C4B—C5B	−2.4 (3)
C2A—C3A—C4A—N2A	−176.5 (2)	C2B—C3B—C4B—N2B	176.7 (2)
C5A—C4A—N2A—O2A	−11.3 (3)	C3B—C4B—N2B—O2B	−167.1 (2)
C3A—C4A—N2A—O2A	167.1 (2)	C5B—C4B—N2B—O2B	12.0 (3)
C5A—C4A—N2A—O1A	169.2 (2)	C3B—C4B—N2B—O1B	12.1 (3)
C3A—C4A—N2A—O1A	−12.4 (3)	C5B—C4B—N2B—O1B	−168.8 (2)
C3A—C4A—C5A—C6A	−0.9 (4)	C3B—C4B—C5B—C6B	1.1 (4)
N2A—C4A—C5A—C6A	177.5 (2)	N2B—C4B—C5B—C6B	−178.0 (2)
C2A—C1A—C6A—C5A	0.1 (4)	C4B—C5B—C6B—C1B	0.9 (4)
N1A—C1A—C6A—C5A	−178.0 (2)	C2B—C1B—C6B—C5B	−1.6 (3)
C4A—C5A—C6A—C1A	−0.1 (4)	N1B—C1B—C6B—C5B	177.4 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A1···F3A	0.89	1.91	2.792 (2)	171
N1A—H1A2···F2B^iii	0.89	2.47	3.088 (2)	127
N1A—H1A2···F3B^iv	0.89	2.01	2.882 (3)	165
N1A—H1A3···F1A^v	0.89	2.57	3.234 (2)	132
N1A—H1A3···F2A^iv	0.89	1.85	2.720 (2)	166
C3A—H3A···O1B^vi	0.93	2.50	3.266 (3)	140
C6A—H6A···F1A	0.93	2.39	3.256 (3)	156
C6A—H6A···F2A	0.93	2.42	3.219 (3)	145
N1B—H1B1···F2B	0.89	2.39	3.031 (2)	130
N1B—H1B1···F3B	0.89	2.13	3.000 (3)	164
N1B—H1B2···F1A^vii	0.89	2.22	2.914 (2)	134
N1B—H1B2···F3A^iii	0.89	2.17	3.018 (2)	159
N1B—H1B3···F1B^iv	0.89	2.06	2.881 (2)	153
N1B—H1B3···F2B^iii	0.89	2.35	3.026 (2)	133
C3B—H3B···O1A^viii	0.93	2.54	3.269 (3)	135

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

(1652)

Crystal data

2(C7H9N2O2)·F6Si·2(H2O	F(000) = 500
Mr = 242.22	Dx = 1.536 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.0445 (8) Å	Cell parameters from 1555 reflections
b = 8.8682 (4) Å	θ = 2.7–23.5°
c = 8.1133 (4) Å	µ = 0.20 mm^−1
β = 104.638 (5)°	T = 295 K
V = 1047.32 (9) Å^3	Plate, yellow
Z = 4	0.32 × 0.29 × 0.01 mm

Data collection

KUMA KM-4 with area CCD detector diffractometer	1117 reflections with I > 2σ(I)
ω–scan	Rint = 0.046
Absorption correction: multi-scan CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	θmax = 23.5°, θmin = 2.7°
Tmin = 0.681, Tmax = 1.000	h = −16→16
8200 measured reflections	k = −9→9
1555 independent reflections	l = −8→9

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.4536P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = <0.001
1555 reflections	Δρmax = 0.28 e Å^−3
150 parameters	Δρmin = −0.24 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
Si1	0.0000	0.0000	0.5000	0.0362 (3)
F1	0.06765 (12)	0.14276 (19)	0.5961 (2)	0.0531 (5)
F2	−0.00753 (12)	0.0786 (2)	0.3116 (2)	0.0572 (6)
F3	0.09301 (12)	−0.09649 (19)	0.4815 (2)	0.0561 (5)
C1	0.22639 (19)	0.3269 (3)	0.4282 (3)	0.0390 (7)
N1	0.13715 (16)	0.3805 (3)	0.4478 (3)	0.0445 (7)
H1A	0.1023	0.4089	0.3468	0.067*
H1B	0.1458	0.4587	0.5189	0.067*
H1C	0.1093	0.3066	0.4894	0.067*
C2	0.2905 (2)	0.4294 (4)	0.4027 (4)	0.0509 (9)
C3	0.3720 (2)	0.3692 (5)	0.3811 (4)	0.0643 (11)
H3	0.4183	0.4333	0.3664	0.077*
C4	0.3847 (2)	0.2168 (5)	0.3813 (4)	0.0571 (10)
N2	0.4714 (3)	0.1580 (6)	0.3516 (5)	0.0897 (12)
O1	0.5362 (2)	0.2402 (5)	0.3735 (6)	0.159 (2)
O2	0.4730 (2)	0.0260 (5)	0.3111 (5)	0.1256 (14)
C5	0.3205 (2)	0.1170 (4)	0.4047 (4)	0.0625 (10)
H5	0.3307	0.0136	0.4042	0.075*
C6	0.2400 (2)	0.1739 (4)	0.4290 (4)	0.0524 (9)
H6	0.1947	0.1088	0.4461	0.063*
C7	0.2733 (3)	0.5961 (4)	0.3940 (6)	0.0899 (14)
H7A	0.2141	0.6161	0.3191	0.135*
H7B	0.3199	0.6453	0.3516	0.135*
H7C	0.2750	0.6335	0.5058	0.135*
O1W	0.1241 (3)	0.6204 (3)	0.6491 (4)	0.0857 (10)
H1W	0.108 (3)	0.701 (3)	0.603 (6)	0.128*
H2W	0.111 (3)	0.615 (6)	0.741 (4)	0.128*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0424 (7)	0.0312 (7)	0.0370 (6)	−0.0035 (6)	0.0141 (5)	0.0008 (5)
F1	0.0622 (12)	0.0470 (11)	0.0527 (11)	−0.0182 (9)	0.0190 (9)	−0.0097 (9)
F2	0.0778 (14)	0.0544 (12)	0.0422 (10)	−0.0057 (10)	0.0204 (9)	0.0108 (9)
F3	0.0522 (11)	0.0475 (11)	0.0749 (13)	0.0078 (9)	0.0280 (9)	0.0042 (9)
C1	0.0346 (18)	0.046 (2)	0.0368 (17)	−0.0039 (15)	0.0097 (14)	0.0006 (14)
N1	0.0471 (16)	0.0453 (15)	0.0422 (14)	−0.0032 (13)	0.0132 (12)	0.0035 (12)
C2	0.045 (2)	0.053 (2)	0.055 (2)	−0.0097 (17)	0.0124 (16)	0.0094 (17)
C3	0.042 (2)	0.081 (3)	0.072 (3)	−0.012 (2)	0.0180 (18)	0.017 (2)
C4	0.039 (2)	0.082 (3)	0.054 (2)	0.011 (2)	0.0173 (16)	0.009 (2)
N2	0.056 (3)	0.122 (4)	0.097 (3)	0.022 (3)	0.032 (2)	0.028 (3)
O1	0.058 (2)	0.154 (4)	0.284 (6)	0.012 (2)	0.075 (3)	0.051 (4)
O2	0.100 (3)	0.147 (4)	0.146 (3)	0.039 (3)	0.061 (2)	−0.020 (3)
C5	0.060 (2)	0.057 (2)	0.077 (3)	0.003 (2)	0.028 (2)	−0.003 (2)
C6	0.047 (2)	0.050 (2)	0.064 (2)	−0.0071 (18)	0.0225 (17)	−0.0045 (17)
C7	0.078 (3)	0.057 (3)	0.141 (4)	−0.013 (2)	0.040 (3)	0.024 (3)
O1W	0.155 (3)	0.0443 (16)	0.076 (2)	0.0150 (17)	0.064 (2)	0.0115 (14)

Geometric parameters (Å, º)

Si1—F2^i	1.6577 (16)	C3—C4	1.365 (5)
Si1—F2	1.6577 (16)	C3—H3	0.9300
Si1—F3^i	1.6789 (17)	C4—C5	1.359 (5)
Si1—F3	1.6790 (17)	C4—N2	1.480 (5)
Si1—F1	1.6868 (16)	N2—O1	1.193 (5)
Si1—F1^i	1.6868 (16)	N2—O2	1.217 (5)
C1—C6	1.372 (4)	C5—C6	1.371 (4)
C1—C2	1.378 (4)	C5—H5	0.9300
C1—N1	1.470 (3)	C6—H6	0.9300
N1—H1A	0.8900	C7—H7A	0.9600
N1—H1B	0.8900	C7—H7B	0.9600
N1—H1C	0.8900	C7—H7C	0.9600
C2—C3	1.389 (5)	O1W—H1W	0.819 (19)
C2—C7	1.499 (5)	O1W—H2W	0.818 (19)
F2^i—Si1—F2	180.0	C1—C2—C7	122.6 (3)
F2^i—Si1—F3^i	89.78 (9)	C3—C2—C7	121.3 (3)
F2—Si1—F3^i	90.22 (9)	C4—C3—C2	120.6 (3)
F2^i—Si1—F3	90.22 (9)	C4—C3—H3	119.7
F2—Si1—F3	89.78 (9)	C2—C3—H3	119.7
F3^i—Si1—F3	180.0	C5—C4—C3	122.7 (3)
F2^i—Si1—F1	89.81 (8)	C5—C4—N2	118.7 (4)
F2—Si1—F1	90.19 (8)	C3—C4—N2	118.6 (4)
F3^i—Si1—F1	89.73 (9)	O1—N2—O2	123.8 (4)
F3—Si1—F1	90.27 (9)	O1—N2—C4	118.7 (5)
F2^i—Si1—F1^i	90.19 (8)	O2—N2—C4	117.4 (4)
F2—Si1—F1^i	89.81 (8)	C4—C5—C6	117.7 (3)
F3^i—Si1—F1^i	90.27 (9)	C4—C5—H5	121.1
F3—Si1—F1^i	89.73 (9)	C6—C5—H5	121.1
F1—Si1—F1^i	180.0	C5—C6—C1	120.0 (3)
C6—C1—C2	122.9 (3)	C5—C6—H6	120.0
C6—C1—N1	117.3 (3)	C1—C6—H6	120.0
C2—C1—N1	119.7 (3)	C2—C7—H7A	109.5
C1—N1—H1A	109.5	C2—C7—H7B	109.5
C1—N1—H1B	109.5	H7A—C7—H7B	109.5
H1A—N1—H1B	109.5	C2—C7—H7C	109.5
C1—N1—H1C	109.5	H7A—C7—H7C	109.5
H1A—N1—H1C	109.5	H7B—C7—H7C	109.5
H1B—N1—H1C	109.5	H1W—O1W—H2W	111 (5)
C1—C2—C3	116.0 (3)
C6—C1—C2—C3	−1.4 (5)	C3—C4—N2—O1	19.7 (6)
N1—C1—C2—C3	−178.4 (3)	C5—C4—N2—O2	16.4 (6)
C6—C1—C2—C7	177.1 (4)	C3—C4—N2—O2	−162.5 (4)
N1—C1—C2—C7	0.1 (5)	C3—C4—C5—C6	0.0 (5)
C1—C2—C3—C4	1.7 (5)	N2—C4—C5—C6	−178.9 (3)
C7—C2—C3—C4	−176.8 (4)	C4—C5—C6—C1	0.4 (5)
C2—C3—C4—C5	−1.0 (6)	C2—C1—C6—C5	0.4 (5)
C2—C3—C4—N2	177.8 (3)	N1—C1—C6—C5	177.5 (3)
C5—C4—N2—O1	−161.4 (4)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F1^ii	0.89	2.02	2.787 (3)	144
N1—H1A···F2^iii	0.89	2.24	3.040 (3)	149
N1—H1B···O1W	0.89	1.86	2.719 (4)	162
N1—H1C···F1	0.89	1.88	2.761 (3)	172
C3—H3···O2^iv	0.93	2.57	3.412 (5)	151
C6—H6···F1	0.93	2.53	3.227 (4)	132
C6—H6···F3	0.93	2.44	3.361 (4)	170
O1W—H1W···F3^v	0.819 (19)	2.03 (2)	2.837 (3)	168 (5)
O1W—H2W···F3^vi	0.818 (19)	2.04 (2)	2.859 (3)	174 (5)

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