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The structure of 1,2-bis(4-pyridyl)­ethyl­enium tris­(malonato-κ2O,O′)­chromate(III) octahydrate, (Hbpe)3[Cr(mal)3]·8H2O, where mal is the malonate dianion (C3HO42−) and bpe is 1,2-bis(4-pyridyl)­ethyl­ene (C12H12N2), is presented. The crystal structure is made up of [Cr(mal)3]3− anions, Hbpe+ cations and water mol­ecules of crystallization. The anions are connected through hydrogen bonding involving malonate O atoms and uncoordinated water mol­ecules in distinct layers, with the cations stacked in separate layers. One of the Hbpe cations is located on a center of inversion, another one on a twofold rotation axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010748/bt6457sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010748/bt6457Isup2.hkl
Contains datablock I

CCDC reference: 242038

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.067
  • wR factor = 0.179
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT213_ALERT_2_B Atom C7D has ADP max/min Ratio ............. 4.20 prolat PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.52 Ratio PLAT250_ALERT_2_B Large U3/U1 Ratio for Average U(i,j) Tensor .... 4.37 PLAT417_ALERT_2_B Short Inter D-H..H-D H2S2 .. H3S1 .. 2.07 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H5S2 .. H7S2 .. 1.92 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H6S2 .. H7S1 .. 2.06 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H6S2 .. H7S2 .. 1.69 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H7S1 .. H8S1 .. 1.76 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H7S1 .. H8S5 .. 1.79 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.43 PLAT213_ALERT_2_C Atom C4D has ADP max/min Ratio ............. 3.70 prolat PLAT213_ALERT_2_C Atom C8D has ADP max/min Ratio ............. 3.20 prolat PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C4D PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C7D PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C6D PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.40 PLAT301_ALERT_3_C Main Residue Disorder ......................... 2.00 Perc. PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 10.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C3D - C4D ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C7D - C8D ... 1.39 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C7D - C8D_b ... 1.39 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 22 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 10 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 11 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 13 H2 O
0 ALERT level A = In general: serious problem 9 ALERT level B = Potentially serious problem 18 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 19 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 5 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

1,2-bis(4-pyridyl)ethylenium tris(malonato-κ2O,O') chromate(III)-water (1/8) top
Crystal data top
(C12H12N2)3[Cr(C3HO4)3]·8H2OF(000) = 4408
Mr = 1051.95Dx = 1.451 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9927 reflections
a = 21.319 (4) Åθ = 2.2–26.0°
b = 11.997 (2) ŵ = 0.32 mm1
c = 38.300 (6) ÅT = 100 K
β = 100.632 (3)°Prism, purple
V = 9628 (3) Å30.50 × 0.19 × 0.12 mm
Z = 8
Data collection top
Bruker APEX
diffractometer
9450 independent reflections
Radiation source: fine-focus sealed tube8293 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 2626
Tmin = 0.855, Tmax = 0.962k = 914
26496 measured reflectionsl = 4747
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.084P)2 + 4P]
where P = (Fo2 + 2Fc2)/3
9450 reflections(Δ/σ)max = 0.002
681 parametersΔρmax = 1.33 e Å3
1 restraintΔρmin = 0.55 e Å3
Special details top

Experimental. The first 50 frames were repeated at the end of data collection and yielded a total of 313 peaks showing a variation of -0.21% during the data collection.

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. The positions of H atoms bonded to carbons and N atoms were determined by geometry and refined by a riding model. H atoms bound to water O atoms were located on a difference map and kept fixed during refinement. The isotropic displacement parameters of the H atoms were set to 1.2 times the isotropic equivalent displacement parameter of the bonded atom.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cr10.12790 (2)0.33273 (4)0.123825 (12)0.01668 (14)
O10.14709 (10)0.33240 (17)0.17627 (5)0.0210 (4)
C20.16217 (13)0.2471 (3)0.19575 (8)0.0204 (6)
C30.17202 (15)0.1343 (3)0.17926 (8)0.0234 (6)
H310.19960.08900.19750.028*
H320.13000.09660.17390.028*
C40.20083 (14)0.1312 (2)0.14571 (8)0.0209 (6)
O50.19192 (9)0.21501 (17)0.12421 (6)0.0212 (4)
O60.16839 (10)0.25136 (18)0.22876 (6)0.0244 (5)
O70.23071 (11)0.04741 (19)0.13980 (6)0.0293 (5)
O80.06180 (9)0.22004 (17)0.12552 (5)0.0194 (4)
C90.05332 (13)0.1316 (3)0.10637 (8)0.0203 (6)
C100.08060 (15)0.1280 (3)0.07231 (8)0.0262 (7)
H1010.05250.07970.05520.031*
H1020.12280.09110.07780.031*
C110.08914 (15)0.2378 (3)0.05359 (8)0.0261 (7)
O120.10756 (10)0.32463 (18)0.07182 (5)0.0239 (5)
O130.02469 (10)0.04890 (18)0.11467 (6)0.0256 (5)
O140.07961 (12)0.2376 (2)0.02069 (6)0.0380 (6)
O150.06468 (9)0.45287 (17)0.12312 (6)0.0208 (4)
C160.07565 (14)0.5535 (3)0.13407 (8)0.0218 (6)
C170.14374 (15)0.5827 (3)0.15199 (9)0.0253 (7)
H1710.14680.66440.15540.030*
H1720.15260.54750.17580.030*
C180.19483 (14)0.5461 (3)0.13145 (8)0.0215 (6)
O190.19342 (10)0.44486 (17)0.12061 (6)0.0219 (4)
O200.03365 (11)0.62526 (19)0.13226 (6)0.0293 (5)
O210.23663 (10)0.61338 (19)0.12724 (6)0.0287 (5)
N1A0.37829 (12)0.4560 (2)0.17383 (6)0.0186 (5)
H1A0.37840.52900.17150.022*
C2A0.42445 (14)0.3934 (2)0.16422 (7)0.0181 (6)
H2A0.45770.42980.15520.022*
C3A0.42604 (13)0.2786 (2)0.16679 (7)0.0166 (6)
H3A0.45980.23750.15980.020*
C4A0.37726 (13)0.2237 (2)0.17984 (7)0.0156 (6)
C5A0.33056 (14)0.2901 (2)0.19078 (8)0.0190 (6)
H5A0.29760.25640.20080.023*
C6A0.33217 (14)0.4046 (2)0.18704 (8)0.0205 (6)
H6A0.29940.44820.19410.025*
C7A0.37281 (13)0.1018 (2)0.18161 (7)0.0165 (6)
H7A0.34240.07150.19420.020*
C8A0.40806 (13)0.0305 (2)0.16692 (7)0.0157 (5)
H8A0.44010.05990.15520.019*
C9A0.40047 (13)0.0908 (2)0.16767 (7)0.0142 (5)
C10A0.44587 (13)0.1603 (2)0.15684 (7)0.0158 (6)
H10A0.48180.12890.14900.019*
C11A0.43865 (13)0.2745 (2)0.15748 (7)0.0160 (6)
H11A0.46960.32160.15020.019*
N12A0.38797 (11)0.31924 (19)0.16843 (6)0.0168 (5)
C13A0.34290 (14)0.2553 (2)0.17868 (8)0.0191 (6)
H13A0.30730.28930.18610.023*
C14A0.34781 (14)0.1410 (2)0.17855 (7)0.0175 (6)
H14A0.31570.09630.18580.021*
N1B0.36790 (13)0.1602 (2)0.07891 (7)0.0212 (5)
H1B0.37120.08720.07790.025*
C2B0.31709 (14)0.2051 (2)0.08971 (7)0.0184 (6)
H2B0.28580.15790.09670.022*
C3B0.30994 (14)0.3186 (2)0.09066 (7)0.0173 (6)
H3B0.27380.34990.09830.021*
C4B0.35593 (14)0.3882 (2)0.08040 (7)0.0182 (6)
C5B0.40913 (15)0.3384 (3)0.07023 (9)0.0242 (7)
H5B0.44190.38340.06380.029*
C6B0.41386 (16)0.2242 (3)0.06953 (9)0.0266 (7)
H6B0.44970.19030.06240.032*
C7B0.34761 (14)0.5092 (2)0.08130 (7)0.0179 (6)
H7B0.31570.53780.09320.021*
C8B0.38227 (13)0.5819 (2)0.06638 (7)0.0181 (6)
H8B0.41320.55240.05390.022*
C9B0.37625 (14)0.7033 (2)0.06773 (7)0.0182 (6)
C10B0.32872 (14)0.7574 (2)0.08221 (7)0.0171 (6)
H10B0.29680.71570.09070.020*
C11B0.32907 (14)0.8727 (2)0.08390 (7)0.0187 (6)
H11B0.29670.90880.09380.022*
N12B0.37304 (12)0.9363 (2)0.07224 (7)0.0222 (5)
C13B0.41734 (16)0.8850 (3)0.05773 (9)0.0275 (7)
H13B0.44820.92920.04910.033*
C14B0.42049 (15)0.7704 (3)0.05456 (8)0.0240 (7)
H14B0.45240.73740.04350.029*
N1C0.24826 (13)0.6392 (2)0.00148 (7)0.0224 (5)
H1C0.25020.71240.00060.027*0.50
C2C0.20590 (16)0.5896 (3)0.01824 (9)0.0277 (7)
H2C0.17870.63470.02940.033*
C3C0.20047 (17)0.4754 (3)0.01984 (9)0.0307 (7)
H3C0.17020.44260.03210.037*
C4C0.23931 (17)0.4093 (3)0.00360 (8)0.0280 (7)
C5C0.28420 (18)0.4617 (3)0.01346 (9)0.0320 (8)
H5C0.31210.41820.02460.038*
C6C0.28775 (16)0.5770 (3)0.01395 (8)0.0265 (7)
H6C0.31840.61230.02530.032*
C7C0.23088 (17)0.2872 (3)0.00536 (9)0.0292 (7)
H7C0.19560.26030.01480.035*
N1D0.50000.3919 (3)0.25000.0192 (7)
H1D0.50000.31860.25000.023*
C2D0.54913 (16)0.4459 (3)0.24098 (8)0.0274 (7)
H2D0.58350.40510.23450.033*
C3D0.5504 (2)0.5605 (3)0.24095 (9)0.0441 (11)
H3D0.58580.59870.23470.053*
C4D0.50000.6203 (4)0.25000.0500 (18)
C5D0.5203 (3)0.7415 (6)0.24589 (15)0.0186 (12)0.50
H5D0.55820.76120.23770.022*0.50
C6D0.4805 (3)0.8160 (5)0.25476 (14)0.0158 (11)0.50
H6D0.44290.79630.26330.019*0.50
C7D0.50000.9375 (4)0.25000.056 (2)
C8D0.4584 (2)0.9971 (3)0.26682 (10)0.0492 (12)
H8D0.42920.95920.27860.059*
C9D0.46006 (16)1.1119 (3)0.26621 (8)0.0279 (7)
H9D0.43151.15200.27790.034*
N10D0.50001.1690 (3)0.25000.0222 (8)
O1S0.22933 (11)0.4412 (2)0.26154 (6)0.0316 (5)
H1S10.20670.39110.24690.038*
H1S20.22280.50190.24810.038*
O2S0.25834 (12)0.1339 (2)0.27427 (6)0.0314 (5)
H2S10.22880.17060.25820.038*
H2S20.28630.19150.27990.038*
O3S0.33754 (13)0.3191 (2)0.28892 (7)0.0389 (6)
H3S10.30440.36100.28350.047*
H3S20.35870.33550.30960.047*
O4S0.06961 (13)0.1514 (2)0.15227 (8)0.0434 (7)
H4S10.09140.14820.13330.052*
H4S20.05490.22120.14420.052*
O5S0.19487 (14)0.1653 (2)0.11021 (9)0.0527 (8)
H5S10.21040.22940.12060.063*
H5S20.16930.18970.09010.063*
O6S0.00988 (15)0.0990 (3)0.01621 (8)0.0577 (8)
H6S10.01800.14810.00500.069*
H6S20.03750.14240.03030.069*
O7S0.10686 (17)0.2240 (3)0.05337 (10)0.0717 (10)
H7S10.08340.28830.04800.086*
H7S20.08110.19580.06780.086*
O8S0.0391 (7)0.4319 (6)0.0497 (2)0.028 (3)0.325 (17)
H8S10.08190.43300.05540.033*0.325 (17)
H8S20.03540.45990.02800.033*0.325 (17)
O8S'0.0371 (3)0.4294 (5)0.00765 (14)0.0165 (13)0.338 (3)
H8S30.04070.47190.01150.020*0.338 (3)
H8S40.03980.36240.00140.020*0.338 (3)
O8S"0.0791 (6)0.4325 (5)0.04916 (16)0.021 (3)0.337 (17)
H8S50.03910.41460.03710.025*0.337 (17)
H8S60.06980.49600.05840.025*0.337 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cr10.0141 (2)0.0118 (2)0.0257 (3)0.00024 (17)0.00763 (18)0.00190 (18)
O10.0234 (11)0.0146 (10)0.0258 (10)0.0003 (8)0.0065 (8)0.0019 (8)
C20.0145 (13)0.0186 (15)0.0289 (15)0.0020 (11)0.0061 (11)0.0009 (12)
C30.0240 (15)0.0157 (15)0.0306 (16)0.0017 (12)0.0053 (12)0.0014 (12)
C40.0171 (14)0.0149 (15)0.0300 (15)0.0013 (12)0.0026 (12)0.0014 (12)
O50.0169 (10)0.0172 (11)0.0311 (11)0.0008 (8)0.0087 (8)0.0015 (9)
O60.0259 (11)0.0229 (11)0.0251 (11)0.0001 (9)0.0063 (9)0.0005 (9)
O70.0295 (12)0.0191 (12)0.0398 (13)0.0059 (10)0.0076 (10)0.0001 (10)
O80.0162 (10)0.0151 (10)0.0289 (11)0.0011 (8)0.0093 (8)0.0006 (8)
C90.0141 (13)0.0195 (15)0.0280 (15)0.0002 (12)0.0054 (11)0.0007 (12)
C100.0241 (16)0.0268 (17)0.0289 (16)0.0014 (13)0.0077 (13)0.0044 (13)
C110.0197 (15)0.0327 (19)0.0276 (16)0.0018 (13)0.0091 (12)0.0004 (14)
O120.0249 (11)0.0243 (12)0.0241 (10)0.0018 (9)0.0089 (9)0.0035 (9)
O130.0259 (11)0.0168 (11)0.0353 (12)0.0031 (9)0.0088 (9)0.0014 (9)
O140.0405 (14)0.0504 (17)0.0242 (12)0.0128 (12)0.0090 (10)0.0002 (11)
O150.0172 (10)0.0130 (10)0.0331 (11)0.0000 (8)0.0074 (8)0.0008 (8)
C160.0195 (14)0.0168 (15)0.0324 (16)0.0006 (12)0.0136 (12)0.0047 (12)
C170.0244 (16)0.0195 (16)0.0342 (17)0.0043 (13)0.0115 (13)0.0036 (13)
C180.0167 (14)0.0197 (16)0.0290 (15)0.0010 (12)0.0067 (12)0.0029 (12)
O190.0170 (10)0.0147 (10)0.0360 (12)0.0007 (8)0.0101 (9)0.0014 (9)
O200.0244 (12)0.0183 (11)0.0487 (14)0.0043 (9)0.0160 (10)0.0012 (10)
O210.0236 (11)0.0200 (12)0.0466 (14)0.0066 (9)0.0170 (10)0.0046 (10)
N1A0.0234 (13)0.0071 (11)0.0254 (12)0.0007 (10)0.0045 (10)0.0012 (9)
C2A0.0202 (14)0.0125 (14)0.0207 (14)0.0037 (11)0.0018 (11)0.0001 (11)
C3A0.0167 (13)0.0120 (14)0.0208 (13)0.0019 (11)0.0024 (11)0.0008 (11)
C4A0.0180 (14)0.0114 (14)0.0159 (12)0.0007 (11)0.0004 (10)0.0009 (10)
C5A0.0219 (15)0.0117 (14)0.0243 (14)0.0004 (11)0.0065 (11)0.0004 (11)
C6A0.0225 (15)0.0133 (14)0.0269 (15)0.0034 (12)0.0074 (12)0.0015 (11)
C7A0.0176 (13)0.0104 (13)0.0208 (13)0.0016 (11)0.0016 (11)0.0018 (11)
C8A0.0155 (13)0.0107 (13)0.0203 (13)0.0025 (11)0.0020 (10)0.0018 (10)
C9A0.0148 (13)0.0120 (13)0.0156 (12)0.0004 (10)0.0023 (10)0.0010 (10)
C10A0.0153 (13)0.0141 (14)0.0180 (13)0.0024 (11)0.0033 (10)0.0012 (10)
C11A0.0179 (13)0.0128 (14)0.0179 (13)0.0018 (11)0.0046 (10)0.0012 (10)
N12A0.0196 (12)0.0109 (11)0.0204 (11)0.0005 (9)0.0049 (9)0.0005 (9)
C13A0.0190 (14)0.0156 (14)0.0256 (14)0.0014 (11)0.0112 (11)0.0006 (11)
C14A0.0188 (14)0.0120 (14)0.0233 (14)0.0001 (11)0.0077 (11)0.0004 (11)
N1B0.0294 (14)0.0095 (12)0.0263 (13)0.0010 (10)0.0094 (11)0.0011 (10)
C2B0.0212 (14)0.0163 (14)0.0178 (13)0.0036 (12)0.0038 (11)0.0013 (11)
C3B0.0191 (14)0.0165 (14)0.0160 (13)0.0004 (11)0.0025 (10)0.0013 (11)
C4B0.0215 (14)0.0171 (15)0.0159 (13)0.0018 (12)0.0029 (11)0.0022 (11)
C5B0.0270 (16)0.0134 (15)0.0356 (17)0.0033 (12)0.0143 (13)0.0013 (12)
C6B0.0291 (17)0.0163 (15)0.0395 (18)0.0010 (13)0.0195 (14)0.0032 (13)
C7B0.0184 (14)0.0143 (14)0.0212 (13)0.0020 (11)0.0046 (11)0.0010 (11)
C8B0.0165 (13)0.0141 (14)0.0239 (14)0.0025 (11)0.0044 (11)0.0016 (11)
C9B0.0226 (15)0.0115 (14)0.0198 (13)0.0018 (11)0.0019 (11)0.0013 (11)
C10B0.0216 (14)0.0117 (13)0.0168 (13)0.0013 (11)0.0009 (11)0.0001 (10)
C11B0.0216 (14)0.0138 (14)0.0205 (14)0.0038 (12)0.0031 (11)0.0020 (11)
N12B0.0261 (13)0.0117 (12)0.0290 (13)0.0022 (10)0.0054 (11)0.0004 (10)
C13B0.0305 (17)0.0161 (16)0.0394 (18)0.0024 (13)0.0157 (14)0.0014 (13)
C14B0.0255 (16)0.0147 (15)0.0340 (16)0.0001 (12)0.0114 (13)0.0017 (12)
N1C0.0322 (14)0.0080 (11)0.0242 (12)0.0008 (10)0.0024 (10)0.0014 (10)
C2C0.0281 (17)0.0173 (16)0.0362 (17)0.0011 (13)0.0019 (13)0.0032 (13)
C3C0.0359 (18)0.0188 (16)0.0359 (18)0.0071 (14)0.0025 (14)0.0052 (13)
C4C0.0403 (19)0.0150 (16)0.0241 (15)0.0044 (14)0.0060 (13)0.0039 (12)
C5C0.050 (2)0.0192 (17)0.0255 (16)0.0113 (15)0.0036 (15)0.0046 (13)
C6C0.0384 (18)0.0155 (15)0.0258 (15)0.0006 (14)0.0064 (13)0.0024 (12)
C7C0.0319 (17)0.0254 (18)0.0297 (16)0.0034 (14)0.0038 (13)0.0025 (13)
N1D0.0284 (19)0.0052 (15)0.0226 (17)0.0000.0008 (14)0.000
C2D0.0281 (17)0.0285 (18)0.0255 (15)0.0056 (14)0.0049 (13)0.0006 (13)
C3D0.065 (3)0.031 (2)0.0303 (18)0.032 (2)0.0060 (17)0.0091 (15)
C4D0.102 (5)0.009 (2)0.025 (2)0.0000.025 (3)0.000
C5D0.018 (3)0.013 (3)0.025 (3)0.002 (2)0.005 (2)0.003 (2)
C6D0.022 (3)0.007 (3)0.019 (3)0.003 (2)0.005 (2)0.001 (2)
C7D0.106 (5)0.008 (2)0.036 (3)0.0000.037 (3)0.000
C8D0.074 (3)0.027 (2)0.0342 (19)0.031 (2)0.0228 (19)0.0147 (16)
C9D0.0296 (17)0.0225 (17)0.0284 (16)0.0033 (14)0.0034 (13)0.0039 (13)
N10D0.030 (2)0.0080 (17)0.0262 (18)0.0000.0018 (15)0.000
O1S0.0392 (13)0.0251 (12)0.0301 (12)0.0085 (10)0.0058 (10)0.0030 (10)
O2S0.0358 (13)0.0243 (12)0.0329 (12)0.0063 (10)0.0028 (10)0.0013 (10)
O3S0.0387 (14)0.0327 (14)0.0452 (15)0.0008 (11)0.0080 (11)0.0039 (11)
O4S0.0355 (14)0.0308 (14)0.0641 (18)0.0004 (11)0.0097 (13)0.0010 (13)
O5S0.0463 (17)0.0338 (16)0.078 (2)0.0045 (13)0.0124 (15)0.0050 (14)
O6S0.0590 (19)0.059 (2)0.0483 (17)0.0164 (16)0.0087 (14)0.0011 (15)
O7S0.064 (2)0.067 (2)0.088 (3)0.0015 (19)0.0240 (19)0.008 (2)
O8S0.028 (8)0.017 (4)0.034 (4)0.005 (3)0.001 (3)0.010 (3)
O8S'0.027 (3)0.010 (3)0.011 (3)0.006 (2)0.002 (2)0.004 (2)
O8S"0.026 (8)0.012 (3)0.024 (3)0.005 (3)0.001 (3)0.006 (2)
Geometric parameters (Å, º) top
Cr1—O191.959 (2)C7B—C8B1.338 (4)
Cr1—O121.961 (2)C7B—H7B0.9500
Cr1—O51.962 (2)C8B—C9B1.464 (4)
Cr1—O81.963 (2)C8B—H8B0.9500
Cr1—O151.970 (2)C9B—C10B1.402 (4)
Cr1—O11.974 (2)C9B—C14B1.403 (4)
O1—C21.273 (4)C10B—C11B1.385 (4)
C2—O61.247 (4)C10B—H10B0.9500
C2—C31.524 (4)C11B—N12B1.347 (4)
C3—C41.524 (4)C11B—H11B0.9500
C3—H310.9900N12B—C13B1.332 (4)
C3—H320.9900C13B—C14B1.383 (4)
C4—O71.233 (4)C13B—H13B0.9500
C4—O51.291 (4)C14B—H14B0.9500
O8—C91.283 (4)N1C—C2C1.340 (4)
C9—O131.237 (4)N1C—C6C1.341 (4)
C9—C101.524 (4)N1C—H1C0.8800
C10—C111.526 (5)C2C—C3C1.377 (5)
C10—H1010.9900C2C—H2C0.9500
C10—H1020.9900C3C—C4C1.376 (5)
C11—O141.239 (4)C3C—H3C0.9500
C11—O121.275 (4)C4C—C5C1.403 (5)
O15—C161.285 (4)C4C—C7C1.479 (5)
C16—O201.235 (4)C5C—C6C1.386 (5)
C16—C171.527 (4)C5C—H5C0.9500
C17—C181.521 (4)C6C—H6C0.9500
C17—H1710.9900C7C—C7Ci1.324 (7)
C17—H1720.9900C7C—H7C0.9500
C18—O211.235 (4)N1D—C2D1.330 (4)
C18—O191.282 (4)N1D—C2Dii1.330 (4)
N1A—C6A1.337 (4)N1D—H1D0.8800
N1A—C2A1.343 (4)C2D—C3D1.375 (5)
N1A—H1A0.8800C2D—H2D0.9500
C2A—C3A1.380 (4)C3D—C4D1.388 (5)
C2A—H2A0.9500C3D—H3D0.9500
C3A—C4A1.399 (4)C4D—C3Dii1.388 (5)
C3A—H3A0.9500C4D—C5D1.533 (8)
C4A—C5A1.398 (4)C5D—C6D1.319 (8)
C4A—C7A1.468 (4)C5D—H5D0.9500
C5A—C6A1.383 (4)C6D—C7D1.535 (7)
C5A—H5A0.9500C6D—H6D0.9500
C6A—H6A0.9500C7D—C8Dii1.387 (6)
C7A—C8A1.330 (4)C7D—C8D1.387 (6)
C7A—H7A0.9500C8D—C9D1.378 (5)
C8A—C9A1.464 (4)C8D—H8D0.9500
C8A—H8A0.9500C9D—N10D1.333 (4)
C9A—C10A1.398 (4)C9D—H9D0.9500
C9A—C14A1.404 (4)N10D—C9Dii1.333 (4)
C10A—C11A1.379 (4)O1S—H1S10.8983
C10A—H10A0.9500O1S—H1S20.8874
C11A—N12A1.341 (4)O2S—H2S10.9094
C11A—H11A0.9500O2S—H2S20.9118
N12A—C13A1.343 (4)O3S—H3S10.8601
C13A—C14A1.375 (4)O3S—H3S20.8598
C13A—H13A0.9500O4S—H4S10.9323
C14A—H14A0.9500O4S—H4S20.9267
N1B—C2B1.342 (4)O5S—H5S10.9009
N1B—C6B1.345 (4)O5S—H5S20.9050
N1B—H1B0.8800O6S—H6S10.8891
C2B—C3B1.372 (4)O6S—H6S20.8917
C2B—H2B0.9500O7S—H7S10.9216
C3B—C4B1.398 (4)O7S—H7S20.9137
C3B—H3B0.9500O8S—H8S10.8987
C4B—C5B1.400 (4)O8S—H8S20.8885
C4B—C7B1.463 (4)O8S'—H8S30.8844
C5B—C6B1.375 (4)O8S'—H8S40.8730
C5B—H5B0.9500O8S"—H8S50.9164
C6B—H6B0.9500O8S"—H8S60.8784
O19—Cr1—O1289.82 (9)C2B—N1B—H1B119.2
O19—Cr1—O589.52 (9)C6B—N1B—H1B119.2
O12—Cr1—O589.72 (9)N1B—C2B—C3B120.5 (3)
O19—Cr1—O8178.32 (9)N1B—C2B—H2B119.8
O12—Cr1—O888.50 (9)C3B—C2B—H2B119.8
O5—Cr1—O890.38 (9)C2B—C3B—C4B119.9 (3)
O19—Cr1—O1589.47 (9)C2B—C3B—H3B120.1
O12—Cr1—O1589.99 (9)C4B—C3B—H3B120.1
O5—Cr1—O15178.95 (9)C3B—C4B—C5B118.0 (3)
O8—Cr1—O1590.62 (8)C3B—C4B—C7B119.4 (3)
O19—Cr1—O192.81 (9)C5B—C4B—C7B122.6 (3)
O12—Cr1—O1176.93 (9)C6B—C5B—C4B119.8 (3)
O5—Cr1—O188.72 (9)C6B—C5B—H5B120.1
O8—Cr1—O188.87 (9)C4B—C5B—H5B120.1
O15—Cr1—O191.61 (9)N1B—C6B—C5B120.3 (3)
C2—O1—Cr1125.50 (19)N1B—C6B—H6B119.9
O6—C2—O1121.9 (3)C5B—C6B—H6B119.9
O6—C2—C3117.4 (3)C8B—C7B—C4B123.9 (3)
O1—C2—C3120.7 (3)C8B—C7B—H7B118.0
C4—C3—C2118.7 (3)C4B—C7B—H7B118.1
C4—C3—H31107.7C7B—C8B—C9B125.1 (3)
C2—C3—H31107.7C7B—C8B—H8B117.5
C4—C3—H32107.7C9B—C8B—H8B117.5
C2—C3—H32107.7C10B—C9B—C14B117.3 (3)
H31—C3—H32107.1C10B—C9B—C8B123.4 (3)
O7—C4—O5122.5 (3)C14B—C9B—C8B119.3 (3)
O7—C4—C3118.5 (3)C11B—C10B—C9B118.9 (3)
O5—C4—C3118.9 (3)C11B—C10B—H10B120.5
C4—O5—Cr1125.84 (19)C9B—C10B—H10B120.5
C9—O8—Cr1125.22 (18)N12B—C11B—C10B123.2 (3)
O13—C9—O8122.7 (3)N12B—C11B—H11B118.4
O13—C9—C10118.8 (3)C10B—C11B—H11B118.4
O8—C9—C10118.5 (3)C13B—N12B—C11B117.9 (3)
C9—C10—C11118.4 (3)N12B—C13B—C14B123.0 (3)
C9—C10—H101107.7N12B—C13B—H13B118.5
C11—C10—H101107.7C14B—C13B—H13B118.5
C9—C10—H102107.7C13B—C14B—C9B119.5 (3)
C11—C10—H102107.7C13B—C14B—H14B120.3
H101—C10—H102107.1C9B—C14B—H14B120.3
O14—C11—O12122.3 (3)C2C—N1C—C6C119.9 (3)
O14—C11—C10117.7 (3)C2C—N1C—H1C120.1
O12—C11—C10119.9 (3)C6C—N1C—H1C120.1
C11—O12—Cr1125.8 (2)N1C—C2C—C3C122.2 (3)
C16—O15—Cr1126.86 (19)N1C—C2C—H2C118.9
O20—C16—O15123.4 (3)C3C—C2C—H2C118.9
O20—C16—C17119.0 (3)C4C—C3C—C2C119.4 (3)
O15—C16—C17117.5 (3)C4C—C3C—H3C120.3
C18—C17—C16114.4 (3)C2C—C3C—H3C120.3
C18—C17—H171108.7C3C—C4C—C5C118.1 (3)
C16—C17—H171108.7C3C—C4C—C7C117.5 (3)
C18—C17—H172108.7C5C—C4C—C7C124.3 (3)
C16—C17—H172108.7C6C—C5C—C4C119.8 (3)
H171—C17—H172107.6C6C—C5C—H5C120.1
O21—C18—O19123.5 (3)C4C—C5C—H5C120.1
O21—C18—C17118.8 (3)N1C—C6C—C5C120.6 (3)
O19—C18—C17117.7 (3)N1C—C6C—H6C119.7
C18—O19—Cr1127.19 (19)C5C—C6C—H6C119.7
C6A—N1A—C2A118.2 (2)C7Ci—C7C—C4C124.5 (4)
C6A—N1A—H1A120.9C7Ci—C7C—H7C117.7
C2A—N1A—H1A120.9C4C—C7C—H7C117.7
N1A—C2A—C3A123.3 (3)C2D—N1D—C2Dii121.8 (4)
N1A—C2A—H2A118.4C2D—N1D—H1D119.1
C3A—C2A—H2A118.4C2Dii—N1D—H1D119.1
C2A—C3A—C4A119.0 (3)N1D—C2D—C3D120.2 (3)
C2A—C3A—H3A120.5N1D—C2D—H2D119.9
C4A—C3A—H3A120.5C3D—C2D—H2D119.9
C5A—C4A—C3A117.2 (3)C2D—C3D—C4D120.0 (4)
C5A—C4A—C7A119.9 (3)C2D—C3D—H3D120.0
C3A—C4A—C7A123.0 (3)C4D—C3D—H3D120.0
C6A—C5A—C4A120.2 (3)C3D—C4D—C3Dii117.7 (4)
C6A—C5A—H5A119.9C3D—C4D—C5D102.7 (3)
C4A—C5A—H5A119.9C3Dii—C4D—C5D139.6 (3)
N1A—C6A—C5A122.1 (3)C6D—C5D—C4D114.2 (5)
N1A—C6A—H6A118.9C6D—C5D—H5D122.9
C5A—C6A—H6A118.9C4D—C5D—H5D122.9
C8A—C7A—C4A125.1 (3)C5D—C6D—C7D114.3 (5)
C8A—C7A—H7A117.4C5D—C6D—H6D122.9
C4A—C7A—H7A117.4C7D—C6D—H6D122.9
C7A—C8A—C9A123.9 (3)C8Dii—C7D—C8D117.9 (5)
C7A—C8A—H8A118.0C8Dii—C7D—C6D139.1 (3)
C9A—C8A—H8A118.0C8D—C7D—C6D102.9 (3)
C10A—C9A—C14A117.8 (3)C9D—C8D—C7D119.2 (4)
C10A—C9A—C8A120.1 (2)C9D—C8D—H8D120.4
C14A—C9A—C8A122.0 (3)C7D—C8D—H8D120.4
C11A—C10A—C9A120.1 (3)N10D—C9D—C8D122.8 (4)
C11A—C10A—H10A119.9N10D—C9D—H9D118.6
C9A—C10A—H10A119.9C8D—C9D—H9D118.6
N12A—C11A—C10A120.1 (3)C9D—N10D—C9Dii118.1 (4)
N12A—C11A—H11A119.9H1S1—O1S—H1S2100.3
C10A—C11A—H11A119.9H2S1—O2S—H2S297.7
C11A—N12A—C13A121.6 (2)H3S1—O3S—H3S2110.9
N12A—C13A—C14A120.6 (3)H4S1—O4S—H4S287.9
N12A—C13A—H13A119.7H5S1—O5S—H5S2102.4
C14A—C13A—H13A119.7H6S1—O6S—H6S2102.4
C13A—C14A—C9A119.7 (3)H7S1—O7S—H7S294.8
C13A—C14A—H14A120.2H8S1—O8S—H8S297.6
C9A—C14A—H14A120.2H8S3—O8S'—H8S4102.2
C2B—N1B—C6B121.5 (3)H8S5—O8S"—H8S698.5
O19—Cr1—O1—C2124.0 (2)C3A—C4A—C7A—C8A9.8 (4)
O8—Cr1—O1—C255.9 (2)C4A—C7A—C8A—C9A177.0 (3)
O15—Cr1—O1—C2146.4 (2)C7A—C8A—C9A—C10A169.5 (3)
Cr1—O1—C2—O6173.8 (2)C7A—C8A—C9A—C14A11.5 (4)
Cr1—O1—C2—C34.9 (4)C14A—C9A—C10A—C11A0.8 (4)
O6—C2—C3—C4146.7 (3)C8A—C9A—C10A—C11A179.9 (3)
O1—C2—C3—C434.5 (4)C9A—C10A—C11A—N12A0.1 (4)
C2—C3—C4—O7152.9 (3)C10A—C11A—N12A—C13A0.6 (4)
C2—C3—C4—O528.6 (4)C11A—N12A—C13A—C14A0.6 (4)
O7—C4—O5—Cr1162.7 (2)N12A—C13A—C14A—C9A0.1 (4)
C3—C4—O5—Cr115.7 (4)C10A—C9A—C14A—C13A0.8 (4)
O19—Cr1—O5—C4133.4 (2)C8A—C9A—C14A—C13A179.9 (3)
O12—Cr1—O5—C4136.8 (2)C6B—N1B—C2B—C3B1.6 (4)
O8—Cr1—O5—C448.3 (2)N1B—C2B—C3B—C4B0.1 (4)
O1—Cr1—O5—C440.6 (2)C2B—C3B—C4B—C5B1.6 (4)
O12—Cr1—O8—C944.0 (2)C2B—C3B—C4B—C7B179.6 (3)
O5—Cr1—O8—C945.7 (2)C3B—C4B—C5B—C6B2.0 (5)
O15—Cr1—O8—C9133.9 (2)C7B—C4B—C5B—C6B179.3 (3)
O1—Cr1—O8—C9134.5 (2)C2B—N1B—C6B—C5B1.1 (5)
Cr1—O8—C9—O13158.8 (2)C4B—C5B—C6B—N1B0.7 (5)
Cr1—O8—C9—C1020.2 (4)C3B—C4B—C7B—C8B167.9 (3)
O13—C9—C10—C11153.7 (3)C5B—C4B—C7B—C8B13.4 (5)
O8—C9—C10—C1127.2 (4)C4B—C7B—C8B—C9B178.2 (3)
C9—C10—C11—O14144.4 (3)C7B—C8B—C9B—C10B6.2 (5)
C9—C10—C11—O1237.9 (4)C7B—C8B—C9B—C14B172.6 (3)
O14—C11—O12—Cr1177.0 (2)C14B—C9B—C10B—C11B2.2 (4)
C10—C11—O12—Cr10.6 (4)C8B—C9B—C10B—C11B176.7 (3)
O19—Cr1—O12—C11146.9 (2)C9B—C10B—C11B—N12B0.0 (4)
O5—Cr1—O12—C1157.4 (2)C10B—C11B—N12B—C13B1.5 (4)
O8—Cr1—O12—C1133.0 (2)C11B—N12B—C13B—C14B0.8 (5)
O15—Cr1—O12—C11123.7 (2)N12B—C13B—C14B—C9B1.4 (5)
O19—Cr1—O15—C1627.8 (2)C10B—C9B—C14B—C13B2.8 (4)
O12—Cr1—O15—C16117.6 (2)C8B—C9B—C14B—C13B176.1 (3)
O8—Cr1—O15—C16153.9 (2)C6C—N1C—C2C—C3C1.0 (5)
O1—Cr1—O15—C1665.0 (2)N1C—C2C—C3C—C4C0.4 (5)
Cr1—O15—C16—O20178.7 (2)C2C—C3C—C4C—C5C1.3 (5)
Cr1—O15—C16—C174.7 (4)C2C—C3C—C4C—C7C178.7 (3)
O20—C16—C17—C18134.0 (3)C3C—C4C—C5C—C6C0.8 (5)
O15—C16—C17—C1849.3 (4)C7C—C4C—C5C—C6C179.2 (3)
C16—C17—C18—O21132.7 (3)C2C—N1C—C6C—C5C1.5 (5)
C16—C17—C18—O1950.0 (4)C4C—C5C—C6C—N1C0.6 (5)
O21—C18—O19—Cr1177.1 (2)C3C—C4C—C7C—C7Ci172.0 (4)
C17—C18—O19—Cr15.7 (4)C5C—C4C—C7C—C7Ci8.0 (6)
O12—Cr1—O19—C18117.3 (2)C2Dii—N1D—C2D—C3D0.3 (2)
O5—Cr1—O19—C18153.0 (3)N1D—C2D—C3D—C4D0.7 (5)
O15—Cr1—O19—C1827.3 (2)C2D—C3D—C4D—C3Dii0.3 (2)
O1—Cr1—O19—C1864.3 (3)C2D—C3D—C4D—C5D179.1 (4)
C6A—N1A—C2A—C3A1.1 (4)C3D—C4D—C5D—C6D177.1 (4)
N1A—C2A—C3A—C4A0.3 (4)C3Dii—C4D—C5D—C6D3.7 (7)
C2A—C3A—C4A—C5A2.2 (4)C4D—C5D—C6D—C7D178.9 (3)
C2A—C3A—C4A—C7A176.3 (3)C5D—C6D—C7D—C8Dii15.1 (7)
C3A—C4A—C5A—C6A2.8 (4)C5D—C6D—C7D—C8D169.5 (4)
C7A—C4A—C5A—C6A175.8 (3)C8Dii—C7D—C8D—C9D0.1 (2)
C2A—N1A—C6A—C5A0.5 (4)C6D—C7D—C8D—C9D176.7 (3)
C4A—C5A—C6A—N1A1.5 (5)C7D—C8D—C9D—N10D0.1 (5)
C5A—C4A—C7A—C8A168.7 (3)C8D—C9D—N10D—C9Dii0.1 (2)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N12Aiii0.881.842.715 (3)174
N1B—H1B···N12Biv0.881.822.702 (4)175
N1C—H1C···N1Cv0.881.782.664 (5)179
N1D—H1D···N10Div0.881.792.674 (5)180
O1S—H1S1···O60.901.942.802 (3)161
O2S—H2S1···O60.911.832.733 (3)176
O2S—H2S2···O3S0.911.882.784 (4)174
O3S—H3S1···O1S0.861.922.770 (4)168
O4S—H4S1···O5S0.932.533.368 (4)149
O4S—H4S2···O20iv0.931.932.853 (4)172
O5S—H5S1···O21iv0.901.972.838 (4)161
O5S—H5S2···O7S0.901.802.692 (5)169
O6S—H6S1···O140.891.842.722 (4)174
O8S—H8S3···O8Svi0.881.872.751 (10)174
O8S—H8S4···O140.871.812.632 (6)156
Symmetry codes: (iii) x, y+1, z; (iv) x, y1, z; (v) x+1/2, y+3/2, z; (vi) x, y+1, z.
 

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