The asymmetric unit of the title compound, [ReO
2(C
5H
6N
2)
4]I·C
5H
6N
2·2H
2O, contains half each of two tetrakis(3-aminopyridine)dioxorhenium(V) cations, an I
− anion, an uncoordinated 3-aminopyridine molecule and two water molecules. Each cation has a centre of inversion at the Re atom. The crystal structure is stabilized by O—H
I, O—H
O, N—H
O, N—H
I and C—H
O hydrogen bonds.
Supporting information
CCDC reference: 618203
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.077
- Data-to-parameter ratio = 30.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.18 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio
PLAT231_ALERT_4_C Hirshfeld Test (Solvent) C32 - C33 .. 7.86 su
PLAT420_ALERT_2_C D-H Without Acceptor N23 - H5A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N23 - H7A ... ?
PLAT420_ALERT_2_C D-H Without Acceptor N24 - H9A ... ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C20 H24 N8 O2 Re
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
2 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); 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 (Bruker, 1999); software used to prepare material for publication: SHELXL97.
Tetrakis(3-aminopyridine-
κN1)dioxorhenium(V) iodide 3-aminopyridine
solvate dihydrate
top
Crystal data top
[ReO2(C5H6N2)4]I·C5H6N2·2H2O | Z = 2 |
Mr = 851.72 | F(000) = 828 |
Triclinic, P1 | Dx = 1.858 Mg m−3 |
a = 9.4860 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.2425 (8) Å | Cell parameters from 2345 reflections |
c = 13.4771 (8) Å | θ = 3.2–25.0° |
α = 81.447 (5)° | µ = 5.05 mm−1 |
β = 70.786 (5)° | T = 100 K |
γ = 72.502 (5)° | Prism, red |
V = 1522.36 (16) Å3 | 0.08 × 0.08 × 0.04 mm |
Data collection top
Kuma KM4-CCD diffractometer | 12818 independent reflections |
Radiation source: fine-focus sealed tube | 8799 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
ω scans | θmax = 36.6°, θmin = 3.2° |
Absorption correction: numerical (CrysAlis RED; Oxford Diffraction, 2004) | h = −13→15 |
Tmin = 0.681, Tmax = 0.826 | k = −21→21 |
27143 measured reflections | l = −20→22 |
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)] = 0.038 | Hydrogen site location: difmap and geom |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0336P)2] where P = (Fo2 + 2Fc2)/3 |
12818 reflections | (Δ/σ)max < 0.001 |
427 parameters | Δρmax = 4.35 e Å−3 |
7 restraints | Δρmin = −2.18 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Re1 | 0.0000 | 0.5000 | 0.5000 | 0.01140 (4) | |
O1 | −0.0430 (2) | 0.60359 (17) | 0.40725 (17) | 0.0146 (4) | |
N1 | 0.2428 (3) | 0.4724 (2) | 0.4153 (2) | 0.0145 (5) | |
C1 | 0.2874 (4) | 0.4932 (2) | 0.3100 (3) | 0.0159 (6) | |
H1 | 0.2100 | 0.5251 | 0.2762 | 0.019* | |
C2 | 0.4428 (4) | 0.4696 (3) | 0.2490 (3) | 0.0181 (6) | |
C3 | 0.5549 (4) | 0.4228 (3) | 0.2993 (3) | 0.0216 (7) | |
H3 | 0.6617 | 0.4054 | 0.2602 | 0.026* | |
C4 | 0.5095 (4) | 0.4019 (3) | 0.4069 (3) | 0.0228 (7) | |
H4 | 0.5851 | 0.3703 | 0.4423 | 0.027* | |
C5 | 0.3530 (4) | 0.4273 (3) | 0.4631 (3) | 0.0197 (7) | |
H5 | 0.3227 | 0.4124 | 0.5371 | 0.024* | |
N21 | 0.4801 (4) | 0.4963 (3) | 0.1418 (3) | 0.0257 (7) | |
N2 | −0.0059 (3) | 0.3877 (2) | 0.4031 (2) | 0.0145 (5) | |
C6 | −0.0339 (4) | 0.4182 (3) | 0.3098 (3) | 0.0166 (6) | |
H6 | −0.0558 | 0.4914 | 0.2883 | 0.020* | |
C7 | −0.0316 (4) | 0.3457 (3) | 0.2441 (3) | 0.0179 (6) | |
H7 | −0.0497 | 0.3695 | 0.1782 | 0.021* | |
C8 | −0.0030 (4) | 0.2391 (3) | 0.2749 (3) | 0.0192 (7) | |
H8 | −0.0036 | 0.1893 | 0.2312 | 0.023* | |
C9 | 0.0266 (4) | 0.2055 (3) | 0.3710 (3) | 0.0166 (6) | |
C10 | 0.0252 (3) | 0.2831 (2) | 0.4321 (3) | 0.0139 (6) | |
H10 | 0.0471 | 0.2611 | 0.4970 | 0.017* | |
N22 | 0.0527 (4) | 0.1010 (2) | 0.4086 (3) | 0.0220 (6) | |
Re2 | −0.5000 | 0.0000 | 0.5000 | 0.01528 (5) | |
O2 | −0.2988 (3) | −0.06049 (18) | 0.47504 (18) | 0.0190 (5) | |
N3 | −0.4779 (3) | 0.1257 (2) | 0.5745 (2) | 0.0184 (6) | |
C11 | −0.3363 (4) | 0.1403 (3) | 0.5587 (3) | 0.0209 (7) | |
H11 | −0.2476 | 0.0967 | 0.5121 | 0.025* | |
C12 | −0.3185 (4) | 0.2174 (3) | 0.6090 (3) | 0.0237 (7) | |
H12 | −0.2184 | 0.2258 | 0.5979 | 0.028* | |
C13 | −0.4462 (5) | 0.2816 (3) | 0.6749 (3) | 0.0257 (8) | |
H13 | −0.4346 | 0.3346 | 0.7095 | 0.031* | |
C14 | −0.5935 (4) | 0.2692 (3) | 0.6913 (3) | 0.0200 (7) | |
C15 | −0.6039 (4) | 0.1887 (3) | 0.6387 (3) | 0.0193 (7) | |
H15 | −0.7029 | 0.1786 | 0.6489 | 0.023* | |
N23 | −0.7266 (4) | 0.3366 (3) | 0.7515 (3) | 0.0263 (7) | |
N4 | −0.4528 (3) | 0.0887 (2) | 0.3518 (2) | 0.0178 (6) | |
C16 | −0.5701 (4) | 0.1632 (3) | 0.3251 (3) | 0.0209 (7) | |
H16 | −0.6720 | 0.1768 | 0.3731 | 0.025* | |
C17 | −0.5434 (4) | 0.2196 (3) | 0.2291 (3) | 0.0233 (7) | |
H17 | −0.6270 | 0.2715 | 0.2118 | 0.028* | |
C18 | −0.3971 (4) | 0.2012 (3) | 0.1583 (3) | 0.0225 (7) | |
H18 | −0.3796 | 0.2401 | 0.0923 | 0.027* | |
C19 | −0.2743 (4) | 0.1249 (3) | 0.1844 (3) | 0.0207 (7) | |
C20 | −0.3092 (4) | 0.0703 (3) | 0.2833 (3) | 0.0185 (7) | |
H20 | −0.2276 | 0.0180 | 0.3026 | 0.022* | |
N24 | −0.1270 (4) | 0.0985 (3) | 0.1151 (3) | 0.0255 (7) | |
N5 | 0.4061 (4) | 0.9051 (2) | 0.1301 (2) | 0.0254 (7) | |
C31 | 0.4565 (5) | 0.8110 (3) | 0.0878 (3) | 0.0313 (9) | |
H31 | 0.3843 | 0.7724 | 0.0929 | 0.038* | |
C32 | 0.6183 (5) | 0.7667 (3) | 0.0346 (3) | 0.0332 (10) | |
C33 | 0.7182 (5) | 0.8282 (3) | 0.0262 (3) | 0.0329 (9) | |
H33 | 0.8252 | 0.8024 | −0.0102 | 0.039* | |
C34 | 0.6669 (6) | 0.9226 (4) | 0.0681 (4) | 0.0399 (10) | |
H34 | 0.7355 | 0.9644 | 0.0615 | 0.048* | |
C35 | 0.5095 (5) | 0.9577 (3) | 0.1217 (3) | 0.0330 (9) | |
H35 | 0.4736 | 1.0234 | 0.1543 | 0.040* | |
N36 | 0.6630 (5) | 0.6694 (3) | −0.0070 (3) | 0.0421 (9) | |
I1 | 0.13012 (3) | 0.62088 (2) | 0.040429 (19) | 0.02421 (6) | |
O3 | 0.0145 (4) | 0.7718 (2) | 0.2651 (2) | 0.0379 (7) | |
O4 | 0.0879 (3) | 0.9686 (2) | 0.2356 (2) | 0.0236 (5) | |
H1A | 0.064 (6) | 0.740 (4) | 0.197 (2) | 0.055 (15)* | |
H2A | 0.010 (7) | 0.710 (3) | 0.315 (4) | 0.071 (18)* | |
H3A | 0.197 (3) | 0.960 (4) | 0.197 (4) | 0.054 (15)* | |
H4A | 0.051 (6) | 0.906 (3) | 0.254 (4) | 0.059 (16)* | |
H5A | −0.795 (6) | 0.308 (4) | 0.767 (4) | 0.031 (13)* | |
H6A | 0.072 (5) | 0.054 (3) | 0.363 (3) | 0.025 (11)* | |
H7A | −0.696 (7) | 0.360 (4) | 0.805 (5) | 0.067 (17)* | |
H8A | 0.559 (6) | 0.457 (4) | 0.105 (4) | 0.043 (14)* | |
H9A | −0.101 (5) | 0.146 (3) | 0.061 (3) | 0.021 (10)* | |
H10A | −0.058 (6) | 0.060 (4) | 0.146 (4) | 0.037 (13)* | |
H11A | 0.097 (5) | 0.083 (3) | 0.453 (4) | 0.028 (12)* | |
H12A | 0.400 (6) | 0.510 (4) | 0.118 (4) | 0.054 (16)* | |
H13A | 0.628 (5) | 0.607 (3) | 0.029 (4) | 0.065* | |
H14A | 0.754 (4) | 0.611 (3) | 0.000 (4) | 0.065* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Re1 | 0.01105 (8) | 0.00994 (8) | 0.01221 (9) | −0.00138 (6) | −0.00334 (7) | −0.00106 (6) |
O1 | 0.0133 (11) | 0.0131 (10) | 0.0161 (11) | −0.0010 (8) | −0.0047 (9) | −0.0015 (8) |
N1 | 0.0143 (13) | 0.0114 (12) | 0.0182 (13) | −0.0019 (10) | −0.0060 (11) | −0.0032 (10) |
C1 | 0.0140 (15) | 0.0120 (14) | 0.0191 (16) | −0.0030 (11) | −0.0017 (12) | −0.0016 (11) |
C2 | 0.0152 (15) | 0.0137 (15) | 0.0221 (17) | −0.0038 (12) | −0.0003 (13) | −0.0037 (12) |
C3 | 0.0107 (15) | 0.0205 (17) | 0.0293 (19) | −0.0018 (12) | −0.0021 (14) | −0.0029 (14) |
C4 | 0.0138 (16) | 0.0251 (18) | 0.0294 (19) | −0.0032 (13) | −0.0087 (14) | −0.0006 (14) |
C5 | 0.0188 (16) | 0.0191 (16) | 0.0210 (17) | −0.0027 (13) | −0.0084 (14) | 0.0003 (13) |
N21 | 0.0170 (15) | 0.0268 (17) | 0.0239 (17) | 0.0002 (13) | 0.0004 (13) | −0.0012 (13) |
N2 | 0.0132 (12) | 0.0136 (13) | 0.0171 (13) | −0.0031 (10) | −0.0048 (11) | −0.0030 (10) |
C6 | 0.0146 (15) | 0.0169 (15) | 0.0183 (16) | −0.0027 (12) | −0.0064 (13) | −0.0009 (12) |
C7 | 0.0140 (15) | 0.0233 (17) | 0.0173 (16) | −0.0038 (13) | −0.0067 (13) | −0.0019 (12) |
C8 | 0.0163 (16) | 0.0195 (16) | 0.0232 (17) | −0.0053 (13) | −0.0048 (14) | −0.0073 (13) |
C9 | 0.0116 (14) | 0.0173 (15) | 0.0199 (16) | −0.0049 (12) | −0.0011 (12) | −0.0046 (12) |
C10 | 0.0104 (13) | 0.0133 (14) | 0.0165 (15) | −0.0017 (11) | −0.0027 (12) | −0.0026 (11) |
N22 | 0.0245 (16) | 0.0138 (14) | 0.0286 (17) | −0.0033 (12) | −0.0101 (14) | −0.0030 (12) |
Re2 | 0.01416 (9) | 0.01330 (9) | 0.01690 (9) | −0.00034 (7) | −0.00534 (7) | −0.00183 (7) |
O2 | 0.0173 (11) | 0.0170 (11) | 0.0205 (12) | −0.0011 (9) | −0.0054 (10) | −0.0023 (9) |
N3 | 0.0215 (14) | 0.0125 (13) | 0.0191 (14) | 0.0003 (11) | −0.0080 (12) | −0.0005 (10) |
C11 | 0.0201 (17) | 0.0205 (17) | 0.0227 (18) | −0.0059 (13) | −0.0087 (14) | 0.0025 (13) |
C12 | 0.0226 (18) | 0.0221 (18) | 0.0267 (19) | −0.0083 (14) | −0.0068 (15) | 0.0013 (14) |
C13 | 0.034 (2) | 0.0196 (18) | 0.031 (2) | −0.0110 (15) | −0.0163 (17) | 0.0001 (14) |
C14 | 0.0272 (18) | 0.0153 (16) | 0.0150 (16) | −0.0026 (13) | −0.0067 (14) | 0.0012 (12) |
C15 | 0.0197 (16) | 0.0162 (16) | 0.0202 (17) | −0.0026 (13) | −0.0059 (13) | 0.0000 (12) |
N23 | 0.0276 (18) | 0.0219 (16) | 0.0276 (18) | −0.0016 (14) | −0.0090 (15) | −0.0051 (13) |
N4 | 0.0178 (14) | 0.0173 (14) | 0.0198 (14) | −0.0036 (11) | −0.0074 (11) | −0.0040 (10) |
C16 | 0.0197 (17) | 0.0153 (16) | 0.0280 (19) | −0.0011 (13) | −0.0109 (14) | −0.0010 (13) |
C17 | 0.0264 (19) | 0.0158 (16) | 0.0295 (19) | −0.0034 (14) | −0.0155 (16) | 0.0048 (13) |
C18 | 0.0296 (19) | 0.0187 (17) | 0.0221 (18) | −0.0106 (14) | −0.0099 (15) | 0.0036 (13) |
C19 | 0.0227 (17) | 0.0182 (16) | 0.0223 (17) | −0.0055 (13) | −0.0076 (14) | −0.0023 (13) |
C20 | 0.0199 (16) | 0.0168 (16) | 0.0198 (17) | −0.0035 (13) | −0.0073 (13) | −0.0036 (12) |
N24 | 0.0222 (16) | 0.0276 (17) | 0.0242 (17) | −0.0070 (13) | −0.0048 (14) | 0.0022 (13) |
N5 | 0.0255 (16) | 0.0215 (15) | 0.0272 (17) | −0.0036 (13) | −0.0077 (13) | −0.0016 (12) |
C31 | 0.044 (2) | 0.0227 (19) | 0.025 (2) | −0.0041 (17) | −0.0118 (18) | −0.0007 (15) |
C32 | 0.055 (3) | 0.0194 (18) | 0.0205 (19) | −0.0007 (18) | −0.0151 (19) | 0.0006 (14) |
C33 | 0.030 (2) | 0.035 (2) | 0.039 (2) | −0.0122 (18) | −0.0201 (19) | 0.0134 (18) |
C34 | 0.045 (3) | 0.048 (3) | 0.035 (2) | −0.021 (2) | −0.017 (2) | 0.002 (2) |
C35 | 0.037 (2) | 0.034 (2) | 0.031 (2) | −0.0121 (18) | −0.0141 (18) | 0.0018 (17) |
N36 | 0.057 (3) | 0.0260 (19) | 0.041 (2) | −0.0011 (17) | −0.020 (2) | −0.0057 (16) |
I1 | 0.01864 (11) | 0.02875 (12) | 0.01841 (11) | −0.00054 (9) | −0.00210 (8) | −0.00095 (8) |
O3 | 0.059 (2) | 0.0232 (15) | 0.0279 (16) | −0.0208 (14) | −0.0006 (15) | −0.0005 (12) |
O4 | 0.0215 (13) | 0.0177 (12) | 0.0300 (14) | −0.0042 (10) | −0.0053 (11) | −0.0040 (10) |
Geometric parameters (Å, º) top
Re1—O1 | 1.761 (2) | C11—H11 | 0.9500 |
Re1—O1i | 1.761 (2) | C12—C13 | 1.369 (5) |
Re1—N2 | 2.144 (3) | C12—H12 | 0.9500 |
Re1—N2i | 2.144 (3) | C13—C14 | 1.397 (5) |
Re1—N1i | 2.151 (3) | C13—H13 | 0.9500 |
Re1—N1 | 2.151 (3) | C14—N23 | 1.383 (5) |
N1—C5 | 1.349 (4) | C14—C15 | 1.408 (5) |
N1—C1 | 1.351 (4) | C15—H15 | 0.9500 |
C1—C2 | 1.396 (4) | N23—H5A | 0.79 (5) |
C1—H1 | 0.9500 | N23—H7A | 0.97 (6) |
C2—N21 | 1.387 (5) | N4—C20 | 1.344 (4) |
C2—C3 | 1.388 (5) | N4—C16 | 1.356 (4) |
C3—C4 | 1.380 (5) | C16—C17 | 1.381 (5) |
C3—H3 | 0.9500 | C16—H16 | 0.9500 |
C4—C5 | 1.388 (5) | C17—C18 | 1.374 (5) |
C4—H4 | 0.9500 | C17—H17 | 0.9500 |
C5—H5 | 0.9500 | C18—C19 | 1.399 (5) |
N21—H8A | 0.82 (5) | C18—H18 | 0.9500 |
N21—H12A | 0.88 (6) | C19—N24 | 1.375 (5) |
N2—C6 | 1.348 (4) | C19—C20 | 1.406 (5) |
N2—C10 | 1.352 (4) | C20—H20 | 0.9500 |
C6—C7 | 1.390 (5) | N24—H9A | 0.91 (4) |
C6—H6 | 0.9500 | N24—H10A | 0.88 (5) |
C7—C8 | 1.381 (5) | N5—C35 | 1.332 (5) |
C7—H7 | 0.9500 | N5—C31 | 1.334 (5) |
C8—C9 | 1.395 (5) | C31—C32 | 1.440 (6) |
C8—H8 | 0.9500 | C31—H31 | 0.9500 |
C9—N22 | 1.379 (4) | C32—N36 | 1.373 (5) |
C9—C10 | 1.405 (4) | C32—C33 | 1.392 (6) |
C10—H10 | 0.9500 | C33—C34 | 1.334 (6) |
N22—H6A | 0.87 (4) | C33—H33 | 0.9500 |
N22—H11A | 0.81 (4) | C34—C35 | 1.393 (6) |
Re2—O2ii | 1.771 (2) | C34—H34 | 0.9500 |
Re2—O2 | 1.771 (2) | C35—H35 | 0.9500 |
Re2—N4 | 2.145 (3) | N36—H13A | 0.98 (4) |
Re2—N4ii | 2.145 (3) | N36—H14A | 0.99 (4) |
Re2—N3ii | 2.160 (3) | O3—H1A | 0.979 (19) |
Re2—N3 | 2.160 (3) | O3—H2A | 0.98 (4) |
N3—C15 | 1.345 (4) | O4—H3A | 0.97 (4) |
N3—C11 | 1.357 (5) | O4—H4A | 0.96 (4) |
C11—C12 | 1.384 (5) | | |
| | | |
O1—Re1—O1i | 180.0 | O2—Re2—N3 | 89.42 (11) |
O1—Re1—N2 | 90.25 (10) | N4—Re2—N3 | 89.59 (10) |
O1i—Re1—N2 | 89.75 (10) | N4ii—Re2—N3 | 90.40 (10) |
O1—Re1—N2i | 89.75 (10) | N3ii—Re2—N3 | 180.0 |
O1i—Re1—N2i | 90.25 (10) | C15—N3—C11 | 119.4 (3) |
N2—Re1—N2i | 180.0 | C15—N3—Re2 | 120.3 (2) |
O1—Re1—N1i | 90.34 (10) | C11—N3—Re2 | 120.3 (2) |
O1i—Re1—N1i | 89.67 (10) | N3—C11—C12 | 121.3 (3) |
N2—Re1—N1i | 92.95 (10) | N3—C11—H11 | 119.3 |
N2i—Re1—N1i | 87.06 (10) | C12—C11—H11 | 119.3 |
O1—Re1—N1 | 89.67 (10) | C13—C12—C11 | 119.6 (3) |
O1i—Re1—N1 | 90.33 (10) | C13—C12—H12 | 120.2 |
N2—Re1—N1 | 87.06 (10) | C11—C12—H12 | 120.2 |
N2i—Re1—N1 | 92.94 (10) | C12—C13—C14 | 120.2 (3) |
N1i—Re1—N1 | 180.0 | C12—C13—H13 | 119.9 |
C5—N1—C1 | 118.6 (3) | C14—C13—H13 | 119.9 |
C5—N1—Re1 | 121.7 (2) | N23—C14—C13 | 122.2 (3) |
C1—N1—Re1 | 119.6 (2) | N23—C14—C15 | 120.1 (3) |
N1—C1—C2 | 122.6 (3) | C13—C14—C15 | 117.6 (3) |
N1—C1—H1 | 118.7 | N3—C15—C14 | 121.9 (3) |
C2—C1—H1 | 118.7 | N3—C15—H15 | 119.1 |
N21—C2—C3 | 122.4 (3) | C14—C15—H15 | 119.1 |
N21—C2—C1 | 119.4 (3) | C14—N23—H5A | 108 (3) |
C3—C2—C1 | 118.1 (3) | C14—N23—H7A | 105 (3) |
C4—C3—C2 | 119.3 (3) | H5A—N23—H7A | 122 (5) |
C4—C3—H3 | 120.3 | C20—N4—C16 | 119.0 (3) |
C2—C3—H3 | 120.3 | C20—N4—Re2 | 121.2 (2) |
C3—C4—C5 | 119.7 (3) | C16—N4—Re2 | 119.7 (2) |
C3—C4—H4 | 120.1 | N4—C16—C17 | 120.8 (3) |
C5—C4—H4 | 120.1 | N4—C16—H16 | 119.6 |
N1—C5—C4 | 121.6 (3) | C17—C16—H16 | 119.6 |
N1—C5—H5 | 119.2 | C18—C17—C16 | 120.7 (3) |
C4—C5—H5 | 119.2 | C18—C17—H17 | 119.7 |
C2—N21—H8A | 116 (3) | C16—C17—H17 | 119.7 |
C2—N21—H12A | 112 (3) | C17—C18—C19 | 119.5 (3) |
H8A—N21—H12A | 113 (5) | C17—C18—H18 | 120.3 |
C6—N2—C10 | 118.0 (3) | C19—C18—H18 | 120.3 |
C6—N2—Re1 | 121.4 (2) | N24—C19—C18 | 122.5 (3) |
C10—N2—Re1 | 120.5 (2) | N24—C19—C20 | 120.4 (3) |
N2—C6—C7 | 122.0 (3) | C18—C19—C20 | 117.1 (3) |
N2—C6—H6 | 119.0 | N4—C20—C19 | 122.9 (3) |
C7—C6—H6 | 119.0 | N4—C20—H20 | 118.5 |
C8—C7—C6 | 119.9 (3) | C19—C20—H20 | 118.5 |
C8—C7—H7 | 120.1 | C19—N24—H9A | 118 (2) |
C6—C7—H7 | 120.1 | C19—N24—H10A | 112 (3) |
C7—C8—C9 | 119.3 (3) | H9A—N24—H10A | 121 (4) |
C7—C8—H8 | 120.4 | C35—N5—C31 | 118.3 (4) |
C9—C8—H8 | 120.4 | N5—C31—C32 | 121.2 (4) |
N22—C9—C8 | 122.9 (3) | N5—C31—H31 | 119.4 |
N22—C9—C10 | 119.5 (3) | C32—C31—H31 | 119.4 |
C8—C9—C10 | 117.6 (3) | N36—C32—C33 | 124.6 (4) |
N2—C10—C9 | 123.2 (3) | N36—C32—C31 | 118.4 (4) |
N2—C10—H10 | 118.4 | C33—C32—C31 | 117.0 (4) |
C9—C10—H10 | 118.4 | C34—C33—C32 | 121.5 (4) |
C9—N22—H6A | 116 (3) | C34—C33—H33 | 119.2 |
C9—N22—H11A | 118 (3) | C32—C33—H33 | 119.2 |
H6A—N22—H11A | 117 (4) | C33—C34—C35 | 117.8 (4) |
O2ii—Re2—O2 | 180.0 | C33—C34—H34 | 121.1 |
O2ii—Re2—N4 | 90.40 (11) | C35—C34—H34 | 121.1 |
O2—Re2—N4 | 89.60 (11) | N5—C35—C34 | 124.2 (4) |
O2ii—Re2—N4ii | 89.60 (11) | N5—C35—H35 | 117.9 |
O2—Re2—N4ii | 90.40 (11) | C34—C35—H35 | 117.9 |
N4—Re2—N4ii | 180.0 | C32—N36—H13A | 125 (3) |
O2ii—Re2—N3ii | 89.42 (11) | C32—N36—H14A | 125 (3) |
O2—Re2—N3ii | 90.58 (11) | H13A—N36—H14A | 71 (4) |
N4—Re2—N3ii | 90.41 (10) | H1A—O3—H2A | 103 (4) |
N4ii—Re2—N3ii | 89.59 (10) | H3A—O4—H4A | 118 (4) |
O2ii—Re2—N3 | 90.58 (11) | | |
| | | |
O1—Re1—N1—C5 | 154.8 (3) | O2ii—Re2—N3—C11 | −163.3 (3) |
O1i—Re1—N1—C5 | −25.2 (3) | O2—Re2—N3—C11 | 16.7 (3) |
N2—Re1—N1—C5 | −114.9 (3) | N4—Re2—N3—C11 | −72.9 (3) |
N2i—Re1—N1—C5 | 65.1 (3) | N4ii—Re2—N3—C11 | 107.1 (3) |
O1—Re1—N1—C1 | −30.2 (2) | C15—N3—C11—C12 | 1.4 (5) |
O1i—Re1—N1—C1 | 149.8 (2) | Re2—N3—C11—C12 | −177.3 (3) |
N2—Re1—N1—C1 | 60.0 (2) | N3—C11—C12—C13 | −1.0 (5) |
N2i—Re1—N1—C1 | −120.0 (2) | C11—C12—C13—C14 | 0.0 (6) |
C5—N1—C1—C2 | 0.1 (5) | C12—C13—C14—N23 | −175.6 (3) |
Re1—N1—C1—C2 | −174.9 (2) | C12—C13—C14—C15 | 0.6 (5) |
N1—C1—C2—N21 | −177.9 (3) | C11—N3—C15—C14 | −0.7 (5) |
N1—C1—C2—C3 | 0.0 (5) | Re2—N3—C15—C14 | 178.0 (2) |
N21—C2—C3—C4 | 177.6 (3) | N23—C14—C15—N3 | 176.0 (3) |
C1—C2—C3—C4 | −0.3 (5) | C13—C14—C15—N3 | −0.3 (5) |
C2—C3—C4—C5 | 0.3 (5) | O2ii—Re2—N4—C20 | −173.1 (3) |
C1—N1—C5—C4 | −0.1 (5) | O2—Re2—N4—C20 | 6.9 (3) |
Re1—N1—C5—C4 | 174.9 (3) | N3ii—Re2—N4—C20 | −83.7 (3) |
C3—C4—C5—N1 | −0.1 (5) | N3—Re2—N4—C20 | 96.3 (3) |
O1—Re1—N2—C6 | 0.9 (2) | O2ii—Re2—N4—C16 | 5.2 (3) |
O1i—Re1—N2—C6 | −179.1 (2) | O2—Re2—N4—C16 | −174.8 (3) |
N1i—Re1—N2—C6 | 91.3 (2) | N3ii—Re2—N4—C16 | 94.7 (3) |
N1—Re1—N2—C6 | −88.7 (2) | N3—Re2—N4—C16 | −85.3 (3) |
O1—Re1—N2—C10 | 178.0 (2) | C20—N4—C16—C17 | 0.0 (5) |
O1i—Re1—N2—C10 | −2.0 (2) | Re2—N4—C16—C17 | −178.4 (3) |
N1i—Re1—N2—C10 | −91.6 (2) | N4—C16—C17—C18 | 0.1 (5) |
N1—Re1—N2—C10 | 88.4 (2) | C16—C17—C18—C19 | −0.3 (5) |
C10—N2—C6—C7 | 0.1 (5) | C17—C18—C19—N24 | 176.3 (3) |
Re1—N2—C6—C7 | 177.2 (2) | C17—C18—C19—C20 | 0.3 (5) |
N2—C6—C7—C8 | 1.3 (5) | C16—N4—C20—C19 | 0.0 (5) |
C6—C7—C8—C9 | −1.4 (5) | Re2—N4—C20—C19 | 178.4 (2) |
C7—C8—C9—N22 | 178.5 (3) | N24—C19—C20—N4 | −176.3 (3) |
C7—C8—C9—C10 | 0.2 (5) | C18—C19—C20—N4 | −0.2 (5) |
C6—N2—C10—C9 | −1.3 (5) | C35—N5—C31—C32 | 0.2 (5) |
Re1—N2—C10—C9 | −178.5 (2) | N5—C31—C32—N36 | 179.8 (4) |
N22—C9—C10—N2 | −177.1 (3) | N5—C31—C32—C33 | −2.2 (6) |
C8—C9—C10—N2 | 1.2 (5) | N36—C32—C33—C34 | 179.6 (4) |
O2ii—Re2—N3—C15 | 18.0 (3) | C31—C32—C33—C34 | 1.8 (6) |
O2—Re2—N3—C15 | −162.0 (3) | C32—C33—C34—C35 | 0.5 (6) |
N4—Re2—N3—C15 | 108.4 (3) | C31—N5—C35—C34 | 2.4 (6) |
N4ii—Re2—N3—C15 | −71.6 (3) | C33—C34—C35—N5 | −2.8 (6) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1A···I1 | 0.98 (3) | 2.62 (4) | 3.558 (3) | 162 (5) |
O3—H2A···O1 | 0.98 (4) | 1.81 (5) | 2.775 (3) | 167 (6) |
O4—H3A···N5 | 0.97 (4) | 1.85 (4) | 2.801 (5) | 164 (4) |
O4—H4A···O3 | 0.96 (5) | 1.89 (4) | 2.835 (4) | 168 (4) |
N22—H6A···O4iii | 0.88 (4) | 2.13 (4) | 2.996 (4) | 167 (4) |
N21—H8A···I1iv | 0.82 (5) | 2.93 (6) | 3.717 (4) | 162 (5) |
N24—H10A···O4iii | 0.88 (6) | 2.12 (6) | 2.999 (5) | 174 (5) |
N22—H11A···O2v | 0.81 (5) | 2.34 (5) | 3.099 (5) | 156 (5) |
N21—H12A···I1 | 0.88 (6) | 2.97 (6) | 3.825 (4) | 163 (4) |
N36—H13A···N21 | 0.98 (4) | 2.37 (5) | 3.320 (6) | 163 (4) |
N36—H14A···I1iv | 0.99 (4) | 3.00 (4) | 3.772 (4) | 135 (3) |
C6—H6···O1 | 0.94 | 2.39 | 2.918 (4) | 114 |
C10—H10···O1i | 0.94 | 2.34 | 2.886 (4) | 115 |
C15—H15···O2ii | 0.95 | 2.44 | 2.955 (5) | 113 |
C16—H16···O2ii | 0.95 | 2.36 | 2.894 (5) | 114 |
C20—H20···O2 | 0.95 | 2.36 | 2.902 (4) | 115 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x−1, −y, −z+1; (iii) x, y−1, z; (iv) −x+1, −y+1, −z; (v) −x, −y, −z+1. |