In the title compound, [Cr(CO
3)(C
16H
36N
4)]Br·H
2O, the chromium cation has a distorted octahedral geometry with ligation provided by the four N atoms of the `folded' macrocyclic ligand and by two O atoms of the bidentate carbonate anion. Two neighbouring chromium complexes are bridged by two strong N—H
O hydrogen bonds to form dimeric units which, in turn, are constituents of infinite chains formed by virtue of three other types of hydrogen bonds (N—H
Br, N—H
Ow and Ow—H
Br).
Supporting information
CCDC reference: 282387
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.005 Å
- R factor = 0.050
- wR factor = 0.117
- Data-to-parameter ratio = 19.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.79
PLAT432_ALERT_2_C Short Inter X...Y Contact O3 .. C10 .. 3.01 Ang.
PLAT731_ALERT_1_C Bond Calc 0.99(4), Rep 0.995(19) ...... 2.11 su-Rat
O4 -H22 1.555 1.555
PLAT748_ALERT_1_C D-H..A Calc 173(4), Rep 173.00 ...... Missing su
O4 -H22 -BR1 1.555 1.555 1.555
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: C17 H38 Br1 Cr1 N4 O4
Atom count from _chemical_formula_moiety:C17 H38 Cr1 N4 O4
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED.
cis-(Carbonato-
κ2O,
O')(rac-5,5,7,12,12,14-hexamethyl-1,4,8,11- tetraazacyclotetradecane-
κ4N)chromium(III) bromide
monohydrate
top
Crystal data top
[Cr(CO3)(C16H36N4)]Br·H2O | Z = 2 |
Mr = 494.42 | F(000) = 518 |
Triclinic, P1 | Dx = 1.511 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.633 (2) Å | Cell parameters from 2358 reflections |
b = 10.924 (3) Å | θ = 2.2–24.4° |
c = 13.296 (4) Å | µ = 2.39 mm−1 |
α = 109.334 (4)° | T = 100 K |
β = 90.305 (5)° | Prism, violet |
γ = 111.828 (4)° | 0.31 × 0.18 × 0.15 mm |
V = 1086.5 (5) Å3 | |
Data collection top
Bruker APEX CCD area-detector diffractometer | 4995 independent reflections |
Radiation source: fine-focus sealed tube | 3792 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −11→11 |
Tmin = 0.594, Tmax = 0.695 | k = −14→14 |
12482 measured reflections | l = −17→17 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0584P)2] where P = (Fo2 + 2Fc2)/3 |
4995 reflections | (Δ/σ)max = 0.001 |
252 parameters | Δρmax = 2.26 e Å−3 |
3 restraints | Δρmin = −0.60 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.70364 (5) | 0.28182 (4) | 0.43268 (3) | 0.02149 (13) | |
Cr1 | 0.24831 (6) | 0.51841 (6) | 0.17639 (4) | 0.00890 (14) | |
O1 | 0.3043 (3) | 0.4147 (2) | 0.04113 (18) | 0.0121 (5) | |
O2 | 0.2189 (3) | 0.5843 (2) | 0.05982 (18) | 0.0118 (5) | |
O3 | 0.2770 (3) | 0.4756 (3) | −0.10281 (18) | 0.0160 (5) | |
O4 | 0.8722 (4) | 0.6243 (3) | 0.5356 (2) | 0.0256 (6) | |
N1 | 0.2721 (3) | 0.3905 (3) | 0.2582 (2) | 0.0122 (6) | |
N4 | 0.5068 (3) | 0.6389 (3) | 0.2318 (2) | 0.0119 (6) | |
N8 | 0.2009 (3) | 0.6703 (3) | 0.3018 (2) | 0.0109 (6) | |
N11 | −0.0157 (3) | 0.4028 (3) | 0.1509 (2) | 0.0103 (6) | |
C2 | 0.4583 (4) | 0.4328 (4) | 0.2802 (3) | 0.0140 (7) | |
C3 | 0.5452 (4) | 0.5909 (4) | 0.3180 (3) | 0.0135 (7) | |
C5 | 0.5810 (4) | 0.7975 (4) | 0.2619 (3) | 0.0135 (7) | |
C6 | 0.4843 (4) | 0.8644 (4) | 0.3422 (3) | 0.0134 (7) | |
C7 | 0.2965 (4) | 0.8198 (4) | 0.3088 (3) | 0.0118 (7) | |
C9 | 0.0159 (4) | 0.6281 (4) | 0.2851 (3) | 0.0141 (7) | |
C10 | −0.0709 (4) | 0.4703 (4) | 0.2533 (3) | 0.0127 (7) | |
C12 | −0.0909 (4) | 0.2426 (4) | 0.1119 (3) | 0.0129 (7) | |
C13 | −0.0101 (4) | 0.1927 (4) | 0.1850 (3) | 0.0147 (7) | |
C14 | 0.1810 (4) | 0.2352 (4) | 0.1978 (3) | 0.0135 (7) | |
C15 | 0.7667 (4) | 0.8616 (4) | 0.3121 (3) | 0.0176 (8) | |
C16 | 0.5746 (5) | 0.8283 (4) | 0.1579 (3) | 0.0175 (8) | |
C17 | 0.2346 (4) | 0.9224 (4) | 0.3902 (3) | 0.0154 (8) | |
C18 | −0.2816 (4) | 0.1876 (4) | 0.1131 (3) | 0.0177 (8) | |
C19 | −0.0609 (5) | 0.1862 (4) | −0.0048 (3) | 0.0166 (8) | |
C20 | 0.2250 (5) | 0.1489 (4) | 0.2557 (3) | 0.0195 (8) | |
C21 | 0.2690 (4) | 0.4912 (4) | −0.0070 (3) | 0.0126 (7) | |
H1 | 0.2318 | 0.4140 | 0.3235 | 0.015* | |
H2A | 0.4994 | 0.3895 | 0.2138 | 0.017* | |
H2B | 0.4841 | 0.3990 | 0.3362 | 0.017* | |
H3A | 0.5052 | 0.6344 | 0.3848 | 0.016* | |
H3B | 0.6686 | 0.6202 | 0.3338 | 0.016* | |
H4 | 0.5613 | 0.6054 | 0.1756 | 0.014* | |
H6A | 0.4974 | 0.8447 | 0.4086 | 0.016* | |
H6B | 0.5396 | 0.9681 | 0.3614 | 0.016* | |
H7 | 0.2797 | 0.8252 | 0.2362 | 0.014* | |
H8 | 0.2302 | 0.6633 | 0.3664 | 0.013* | |
H9A | −0.0203 | 0.6754 | 0.3524 | 0.017* | |
H9B | −0.0154 | 0.6575 | 0.2278 | 0.017* | |
H10A | −0.1948 | 0.4410 | 0.2428 | 0.015* | |
H10B | −0.0407 | 0.4407 | 0.3107 | 0.015* | |
H11 | −0.0588 | 0.4259 | 0.0988 | 0.012* | |
H13A | −0.0404 | 0.2269 | 0.2578 | 0.018* | |
H13B | −0.0639 | 0.0882 | 0.1580 | 0.018* | |
H14 | 0.2157 | 0.2117 | 0.1246 | 0.016* | |
H15A | 0.7754 | 0.8421 | 0.3782 | 0.026* | |
H15B | 0.8306 | 0.8198 | 0.2609 | 0.026* | |
H15C | 0.8129 | 0.9640 | 0.3292 | 0.026* | |
H16A | 0.6375 | 0.7836 | 0.1080 | 0.026* | |
H16B | 0.6253 | 0.9306 | 0.1747 | 0.026* | |
H16C | 0.4570 | 0.7903 | 0.1245 | 0.026* | |
H17A | 0.2978 | 1.0185 | 0.3916 | 0.023* | |
H17B | 0.1142 | 0.8949 | 0.3687 | 0.023* | |
H17C | 0.2525 | 0.9194 | 0.4620 | 0.023* | |
H18A | −0.3042 | 0.2239 | 0.1869 | 0.027* | |
H18B | −0.3333 | 0.2197 | 0.0666 | 0.027* | |
H18C | −0.3293 | 0.0841 | 0.0865 | 0.027* | |
H19A | −0.1134 | 0.2201 | −0.0494 | 0.025* | |
H19B | −0.1107 | 0.0827 | −0.0321 | 0.025* | |
H19C | 0.0606 | 0.2197 | −0.0077 | 0.025* | |
H20A | 0.1886 | 0.1688 | 0.3269 | 0.029* | |
H20B | 0.1673 | 0.0480 | 0.2131 | 0.029* | |
H20C | 0.3472 | 0.1750 | 0.2639 | 0.029* | |
H22 | 0.829 (6) | 0.520 (2) | 0.501 (5) | 0.10 (2)* | |
H23 | 0.992 (2) | 0.662 (4) | 0.553 (4) | 0.058 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0215 (2) | 0.0253 (2) | 0.0176 (2) | 0.00562 (17) | 0.00318 (15) | 0.01172 (17) |
Cr1 | 0.0091 (3) | 0.0095 (3) | 0.0086 (3) | 0.0039 (2) | 0.0024 (2) | 0.0036 (2) |
O1 | 0.0142 (13) | 0.0151 (13) | 0.0103 (12) | 0.0089 (10) | 0.0045 (10) | 0.0049 (10) |
O2 | 0.0120 (12) | 0.0145 (13) | 0.0113 (12) | 0.0070 (10) | 0.0027 (9) | 0.0055 (10) |
O3 | 0.0178 (13) | 0.0219 (14) | 0.0092 (12) | 0.0092 (11) | 0.0024 (10) | 0.0053 (11) |
O4 | 0.0249 (16) | 0.0289 (18) | 0.0212 (15) | 0.0114 (13) | 0.0057 (12) | 0.0060 (13) |
N1 | 0.0100 (15) | 0.0149 (16) | 0.0127 (15) | 0.0055 (12) | 0.0024 (11) | 0.0058 (12) |
N4 | 0.0107 (15) | 0.0127 (15) | 0.0130 (14) | 0.0048 (12) | 0.0045 (11) | 0.0051 (12) |
N8 | 0.0101 (14) | 0.0139 (15) | 0.0104 (14) | 0.0053 (12) | 0.0019 (11) | 0.0060 (12) |
N11 | 0.0101 (14) | 0.0101 (15) | 0.0101 (14) | 0.0032 (12) | 0.0013 (11) | 0.0040 (12) |
C2 | 0.0097 (17) | 0.0191 (19) | 0.0140 (17) | 0.0065 (15) | 0.0010 (13) | 0.0062 (15) |
C3 | 0.0106 (17) | 0.0183 (19) | 0.0144 (18) | 0.0082 (15) | 0.0031 (14) | 0.0061 (15) |
C5 | 0.0116 (17) | 0.0128 (18) | 0.0156 (18) | 0.0036 (14) | 0.0032 (14) | 0.0060 (15) |
C6 | 0.0140 (18) | 0.0095 (18) | 0.0155 (18) | 0.0050 (14) | 0.0021 (14) | 0.0027 (14) |
C7 | 0.0115 (17) | 0.0096 (17) | 0.0140 (17) | 0.0031 (14) | 0.0026 (14) | 0.0051 (14) |
C9 | 0.0115 (17) | 0.0170 (19) | 0.0125 (17) | 0.0062 (15) | 0.0020 (13) | 0.0032 (15) |
C10 | 0.0122 (17) | 0.0148 (19) | 0.0101 (17) | 0.0049 (15) | 0.0031 (13) | 0.0035 (14) |
C12 | 0.0137 (18) | 0.0097 (18) | 0.0126 (17) | 0.0014 (14) | 0.0003 (14) | 0.0043 (14) |
C13 | 0.0161 (19) | 0.0125 (19) | 0.0163 (18) | 0.0054 (15) | 0.0029 (14) | 0.0063 (15) |
C14 | 0.0136 (18) | 0.0119 (18) | 0.0158 (18) | 0.0049 (15) | 0.0055 (14) | 0.0059 (15) |
C15 | 0.0124 (18) | 0.015 (2) | 0.0209 (19) | 0.0043 (15) | 0.0017 (15) | 0.0031 (16) |
C16 | 0.0178 (19) | 0.018 (2) | 0.0189 (19) | 0.0056 (16) | 0.0072 (15) | 0.0102 (16) |
C17 | 0.0102 (17) | 0.0139 (19) | 0.0205 (19) | 0.0061 (15) | 0.0002 (14) | 0.0026 (15) |
C18 | 0.0105 (18) | 0.021 (2) | 0.023 (2) | 0.0046 (15) | 0.0025 (15) | 0.0105 (17) |
C19 | 0.021 (2) | 0.0124 (19) | 0.0125 (18) | 0.0051 (16) | 0.0022 (15) | 0.0020 (15) |
C20 | 0.024 (2) | 0.016 (2) | 0.022 (2) | 0.0099 (17) | 0.0024 (16) | 0.0082 (16) |
C21 | 0.0066 (16) | 0.0131 (18) | 0.0139 (18) | 0.0006 (14) | 0.0012 (13) | 0.0035 (14) |
Geometric parameters (Å, º) top
Cr1—O1 | 1.954 (2) | C14—C20 | 1.539 (5) |
Cr1—O2 | 1.964 (2) | C14—H14 | 1.0000 |
Cr1—N8 | 2.093 (3) | C3—H3A | 0.9900 |
Cr1—N1 | 2.096 (3) | C3—H3B | 0.9900 |
Cr1—N4 | 2.100 (3) | C9—C10 | 1.505 (5) |
Cr1—N11 | 2.115 (3) | C9—H9B | 0.9900 |
O1—C21 | 1.319 (4) | C9—H9A | 0.9900 |
O3—C21 | 1.234 (4) | C19—H19A | 0.9800 |
N8—C9 | 1.481 (4) | C19—H19B | 0.9800 |
N8—C7 | 1.500 (4) | C19—H19C | 0.9800 |
N8—H8 | 0.9300 | C10—H10B | 0.9900 |
O4—H22 | 0.995 (19) | C10—H10A | 0.9900 |
O4—H23 | 0.953 (19) | C18—H18B | 0.9800 |
N1—C2 | 1.495 (4) | C18—H18A | 0.9800 |
N1—C14 | 1.496 (4) | C18—H18C | 0.9800 |
N1—H1 | 0.9300 | C20—H20C | 0.9800 |
O2—C21 | 1.321 (4) | C20—H20B | 0.9800 |
N11—C10 | 1.492 (4) | C20—H20A | 0.9800 |
N11—C12 | 1.518 (4) | C13—H13A | 0.9900 |
N11—H11 | 0.9300 | C13—H13B | 0.9900 |
N4—C3 | 1.491 (4) | C7—C6 | 1.525 (5) |
N4—C5 | 1.511 (4) | C7—H7 | 1.0000 |
N4—H4 | 0.9300 | C5—C6 | 1.523 (5) |
C17—C7 | 1.537 (5) | C5—C16 | 1.532 (5) |
C17—H17B | 0.9800 | C5—C15 | 1.533 (5) |
C17—H17A | 0.9800 | C6—H6B | 0.9900 |
C17—H17C | 0.9800 | C6—H6A | 0.9900 |
C2—C3 | 1.502 (5) | C15—H15B | 0.9800 |
C2—H2A | 0.9900 | C15—H15A | 0.9800 |
C2—H2B | 0.9900 | C15—H15C | 0.9800 |
C12—C18 | 1.530 (5) | C16—H16A | 0.9800 |
C12—C19 | 1.531 (5) | C16—H16B | 0.9800 |
C12—C13 | 1.536 (5) | C16—H16C | 0.9800 |
C14—C13 | 1.530 (5) | | |
| | | |
O1—Cr1—O2 | 67.59 (10) | C2—C3—H3A | 109.9 |
O1—Cr1—N8 | 164.48 (10) | N4—C3—H3B | 109.9 |
O2—Cr1—N8 | 97.91 (10) | C2—C3—H3B | 109.9 |
O1—Cr1—N1 | 95.06 (11) | H3A—C3—H3B | 108.3 |
O2—Cr1—N1 | 161.49 (11) | N8—C9—C10 | 109.3 (3) |
N8—Cr1—N1 | 99.92 (11) | N8—C9—H9B | 109.8 |
O1—Cr1—N4 | 89.37 (11) | C10—C9—H9B | 109.8 |
O2—Cr1—N4 | 99.97 (10) | N8—C9—H9A | 109.8 |
N8—Cr1—N4 | 87.74 (11) | C10—C9—H9A | 109.8 |
N1—Cr1—N4 | 85.68 (11) | H9B—C9—H9A | 108.3 |
O1—Cr1—N11 | 99.68 (10) | C12—C19—H19A | 109.5 |
O2—Cr1—N11 | 88.64 (10) | C12—C19—H19B | 109.5 |
N8—Cr1—N11 | 84.96 (11) | H19A—C19—H19B | 109.5 |
N1—Cr1—N11 | 88.03 (11) | C12—C19—H19C | 109.5 |
N4—Cr1—N11 | 169.41 (11) | H19A—C19—H19C | 109.5 |
C21—O1—Cr1 | 90.80 (19) | H19B—C19—H19C | 109.5 |
C9—N8—C7 | 112.3 (3) | N11—C10—C9 | 108.3 (3) |
C9—N8—Cr1 | 105.4 (2) | N11—C10—H10B | 110.0 |
C7—N8—Cr1 | 114.6 (2) | C9—C10—H10B | 110.0 |
C9—N8—H8 | 108.1 | N11—C10—H10A | 110.0 |
C7—N8—H8 | 108.1 | C9—C10—H10A | 110.0 |
Cr1—N8—H8 | 108.1 | H10B—C10—H10A | 108.4 |
H22—O4—H23 | 109 (3) | C12—C18—H18B | 109.5 |
C2—N1—C14 | 112.0 (3) | C12—C18—H18A | 109.5 |
C2—N1—Cr1 | 104.1 (2) | H18B—C18—H18A | 109.5 |
C14—N1—Cr1 | 114.5 (2) | C12—C18—H18C | 109.5 |
C2—N1—H1 | 108.7 | H18B—C18—H18C | 109.5 |
C14—N1—H1 | 108.7 | H18A—C18—H18C | 109.5 |
Cr1—N1—H1 | 108.7 | C14—C20—H20C | 109.5 |
C21—O2—Cr1 | 90.33 (19) | C14—C20—H20B | 109.5 |
C10—N11—C12 | 113.5 (3) | H20C—C20—H20B | 109.5 |
C10—N11—Cr1 | 104.00 (19) | C14—C20—H20A | 109.5 |
C12—N11—Cr1 | 121.1 (2) | H20C—C20—H20A | 109.5 |
C10—N11—H11 | 105.7 | H20B—C20—H20A | 109.5 |
C12—N11—H11 | 105.7 | C14—C13—C12 | 119.3 (3) |
Cr1—N11—H11 | 105.7 | C14—C13—H13A | 107.5 |
C3—N4—C5 | 114.1 (3) | C12—C13—H13A | 107.5 |
C3—N4—Cr1 | 104.4 (2) | C14—C13—H13B | 107.5 |
C5—N4—Cr1 | 121.3 (2) | C12—C13—H13B | 107.5 |
C3—N4—H4 | 105.2 | H13A—C13—H13B | 107.0 |
C5—N4—H4 | 105.2 | N8—C7—C6 | 110.1 (3) |
Cr1—N4—H4 | 105.2 | N8—C7—C17 | 111.6 (3) |
O3—C21—O1 | 124.7 (3) | C6—C7—C17 | 109.1 (3) |
O3—C21—O2 | 124.0 (3) | N8—C7—H7 | 108.7 |
O1—C21—O2 | 111.3 (3) | C6—C7—H7 | 108.7 |
C7—C17—H17B | 109.5 | C17—C7—H7 | 108.7 |
C7—C17—H17A | 109.5 | N4—C5—C6 | 110.6 (3) |
H17B—C17—H17A | 109.5 | N4—C5—C16 | 107.7 (3) |
C7—C17—H17C | 109.5 | C6—C5—C16 | 111.5 (3) |
H17B—C17—H17C | 109.5 | N4—C5—C15 | 110.9 (3) |
H17A—C17—H17C | 109.5 | C6—C5—C15 | 108.6 (3) |
N1—C2—C3 | 109.3 (3) | C16—C5—C15 | 107.4 (3) |
N1—C2—H2A | 109.8 | C5—C6—C7 | 118.2 (3) |
C3—C2—H2A | 109.8 | C5—C6—H6B | 107.7 |
N1—C2—H2B | 109.8 | C7—C6—H6B | 107.7 |
C3—C2—H2B | 109.8 | C5—C6—H6A | 107.7 |
H2A—C2—H2B | 108.3 | C7—C6—H6A | 107.7 |
N11—C12—C18 | 110.1 (3) | H6B—C6—H6A | 107.1 |
N11—C12—C19 | 108.2 (3) | C5—C15—H15B | 109.5 |
C18—C12—C19 | 107.9 (3) | C5—C15—H15A | 109.5 |
N11—C12—C13 | 109.9 (3) | H15B—C15—H15A | 109.5 |
C18—C12—C13 | 109.4 (3) | C5—C15—H15C | 109.5 |
C19—C12—C13 | 111.4 (3) | H15B—C15—H15C | 109.5 |
N1—C14—C13 | 111.0 (3) | H15A—C15—H15C | 109.5 |
N1—C14—C20 | 111.2 (3) | C5—C16—H16A | 109.5 |
C13—C14—C20 | 108.8 (3) | C5—C16—H16B | 109.5 |
N1—C14—H14 | 108.6 | H16A—C16—H16B | 109.5 |
C13—C14—H14 | 108.6 | C5—C16—H16C | 109.5 |
C20—C14—H14 | 108.6 | H16A—C16—H16C | 109.5 |
N4—C3—C2 | 108.8 (3) | H16B—C16—H16C | 109.5 |
N4—C3—H3A | 109.9 | | |
| | | |
O2—Cr1—O1—C21 | 0.43 (18) | N8—Cr1—N4—C5 | −45.2 (2) |
N8—Cr1—O1—C21 | −21.4 (5) | N1—Cr1—N4—C5 | −145.4 (2) |
N1—Cr1—O1—C21 | 173.76 (19) | N11—Cr1—N4—C5 | −91.6 (6) |
N4—Cr1—O1—C21 | −100.63 (19) | Cr1—O1—C21—O3 | −178.7 (3) |
N11—Cr1—O1—C21 | 84.9 (2) | Cr1—O1—C21—O2 | −0.6 (3) |
O1—Cr1—N8—C9 | 95.5 (4) | Cr1—O2—C21—O3 | 178.8 (3) |
O2—Cr1—N8—C9 | 75.2 (2) | Cr1—O2—C21—O1 | 0.6 (3) |
N1—Cr1—N8—C9 | −99.9 (2) | C14—N1—C2—C3 | 167.5 (3) |
N4—Cr1—N8—C9 | 174.9 (2) | Cr1—N1—C2—C3 | 43.2 (3) |
N11—Cr1—N8—C9 | −12.7 (2) | C10—N11—C12—C18 | 48.7 (4) |
O1—Cr1—N8—C7 | −28.6 (5) | Cr1—N11—C12—C18 | 173.4 (2) |
O2—Cr1—N8—C7 | −48.9 (2) | C10—N11—C12—C19 | 166.4 (3) |
N1—Cr1—N8—C7 | 136.1 (2) | Cr1—N11—C12—C19 | −68.9 (3) |
N4—Cr1—N8—C7 | 50.9 (2) | C10—N11—C12—C13 | −71.8 (3) |
N11—Cr1—N8—C7 | −136.8 (2) | Cr1—N11—C12—C13 | 52.9 (3) |
O1—Cr1—N1—C2 | 73.9 (2) | C2—N1—C14—C13 | 175.0 (3) |
O2—Cr1—N1—C2 | 93.7 (4) | Cr1—N1—C14—C13 | −66.8 (3) |
N8—Cr1—N1—C2 | −102.0 (2) | C2—N1—C14—C20 | 53.7 (4) |
N4—Cr1—N1—C2 | −15.1 (2) | Cr1—N1—C14—C20 | 171.9 (2) |
N11—Cr1—N1—C2 | 173.5 (2) | C5—N4—C3—C2 | 177.4 (3) |
O1—Cr1—N1—C14 | −48.7 (2) | Cr1—N4—C3—C2 | 42.8 (3) |
O2—Cr1—N1—C14 | −29.0 (4) | N1—C2—C3—N4 | −60.4 (3) |
N8—Cr1—N1—C14 | 135.3 (2) | C7—N8—C9—C10 | 167.0 (3) |
N4—Cr1—N1—C14 | −137.7 (2) | Cr1—N8—C9—C10 | 41.5 (3) |
N11—Cr1—N1—C14 | 50.8 (2) | C12—N11—C10—C9 | 178.3 (3) |
O1—Cr1—O2—C21 | −0.43 (18) | Cr1—N11—C10—C9 | 44.8 (3) |
N8—Cr1—O2—C21 | 173.80 (19) | N8—C9—C10—N11 | −60.4 (3) |
N1—Cr1—O2—C21 | −21.8 (4) | N1—C14—C13—C12 | 68.5 (4) |
N4—Cr1—O2—C21 | 84.7 (2) | C20—C14—C13—C12 | −168.8 (3) |
N11—Cr1—O2—C21 | −101.48 (19) | N11—C12—C13—C14 | −58.7 (4) |
O1—Cr1—N11—C10 | 177.48 (19) | C18—C12—C13—C14 | −179.6 (3) |
O2—Cr1—N11—C10 | −115.5 (2) | C19—C12—C13—C14 | 61.3 (4) |
N8—Cr1—N11—C10 | −17.5 (2) | C9—N8—C7—C6 | 171.7 (3) |
N1—Cr1—N11—C10 | 82.7 (2) | Cr1—N8—C7—C6 | −68.0 (3) |
N4—Cr1—N11—C10 | 29.1 (7) | C9—N8—C7—C17 | 50.5 (4) |
O1—Cr1—N11—C12 | 48.5 (2) | Cr1—N8—C7—C17 | 170.8 (2) |
O2—Cr1—N11—C12 | 115.5 (2) | C3—N4—C5—C6 | −73.5 (3) |
N8—Cr1—N11—C12 | −146.4 (2) | Cr1—N4—C5—C6 | 52.7 (3) |
N1—Cr1—N11—C12 | −46.3 (2) | C3—N4—C5—C16 | 164.3 (3) |
N4—Cr1—N11—C12 | −99.9 (6) | Cr1—N4—C5—C16 | −69.4 (3) |
O1—Cr1—N4—C3 | −110.0 (2) | C3—N4—C5—C15 | 47.1 (4) |
O2—Cr1—N4—C3 | −177.1 (2) | Cr1—N4—C5—C15 | 173.3 (2) |
N8—Cr1—N4—C3 | 85.3 (2) | N4—C5—C6—C7 | −59.6 (4) |
N1—Cr1—N4—C3 | −14.9 (2) | C16—C5—C6—C7 | 60.2 (4) |
N11—Cr1—N4—C3 | 38.9 (7) | C15—C5—C6—C7 | 178.4 (3) |
O1—Cr1—N4—C5 | 119.5 (2) | N8—C7—C6—C5 | 69.8 (4) |
O2—Cr1—N4—C5 | 52.4 (2) | C17—C7—C6—C5 | −167.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N8—H8···Br1i | 0.93 | 2.55 | 3.441 (3) | 161 |
N1—H1···O4i | 0.93 | 2.18 | 3.045 (4) | 155 |
N11—H11···O2ii | 0.93 | 2.46 | 3.368 (4) | 164 |
N11—H11···O3ii | 0.93 | 2.49 | 3.168 (4) | 130 |
N4—H4···O3iii | 0.93 | 2.01 | 2.888 (4) | 157 |
O4—H22···Br1 | 0.99 (4) | 2.26 (4) | 3.245 (3) | 173 |
O4—H23···Br1iv | 0.95 (3) | 2.46 (2) | 3.398 (4) | 169 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z+1. |