Calcium anilate hexa­hydrate

Schmidt, M.U.; Schmiermund, T.; Bolte, M.

doi:10.1107/S160053680605553X

Calcium anilate hexahydrate

M. U. Schmidt, T. Schmiermund and M. Bolte

Anilic acid or 2,5-dianilinoterephthalic acid, C₂₀H₁₆N₂O₄, is an intermediate in the industrial synthesis of quinacridone pigments. The title calcium aniloate compound, namely di-μ-aqua-κ⁴O¹:O^1′-bis(μ-2,5-dianilinoterephthalo-κ²O:O′)bis[triaquacalcium(II)] tetrahydrate, [Ca₂(C₂₀H₁₄N₂O₄)₂(H₂O)₈]·4H₂O, is a dimeric complex of two aniloate anions, two Ca²⁺ cations and eight water molecules, with a further four uncoordinated water molecules. The complex is situated on a crystallographic twofold axis, with two water O atoms lying on the rotation axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605553X/hb2239sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680605553X/hb2239Isup2.hkl Contains datablock I

CCDC reference: 638511

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.008 Å
H-atom completeness 74%
Disorder in solvent or counterion
R factor = 0.098
wR factor = 0.275
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) .......        O1W

Author Response: The H could not be located in a difference map and were excluded from the refinement.

PLAT430_ALERT_2_A Short Inter D...A Contact  O2W'   ..  O2W'    ..       2.27 Ang.

Author Response: This water O atoms is disordered over two sites.


Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1W    ..  O2W'    ..       2.68 Ang.

Author Response: This water O atoms is disordered over two sites.

PLAT430_ALERT_2_B Short Inter D...A Contact  O1W    ..  O11     ..       2.77 Ang.

Author Response: This water O atoms is disordered over two sites.

PLAT731_ALERT_1_B Bond    Calc     0.85(7), Rep   0.839(11) ......       6.36 su-Ra
              O1   -H1A     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.84(7), Rep   0.842(10) ......       7.00 su-Ra
              O2   -H2A     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Ra
              O4   -H4A     1.555   1.555
PLAT731_ALERT_1_B Bond    Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Ra
              O5   -H5A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.85(7), Rep   0.839(11) ......       6.36 su-Ra
              O1   -H1A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(7), Rep   0.842(10) ......       7.00 su-Ra
              O2   -H2A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Ra
              O4   -H4A     1.555   1.555
PLAT735_ALERT_1_B D-H     Calc     0.84(5), Rep   0.840(10) ......       5.00 su-Ra
              O5   -H5A     1.555   1.555

Alert level C
CHEMW03_ALERT_2_C The ratio of given/expected molecular weight as
            calculated from the _atom_site* data lies outside
            the range 0.99 <> 1.01
           From the CIF: _cell_formula_units_Z                    4
           From the CIF: _chemical_formula_weight           989.02
           TEST: Calculate formula weight from _atom_site_*
           atom     mass    num     sum
           C        12.01   40.00  480.44
           H         1.01   38.00   38.30
           Ca       40.08    2.00   80.16
           N        14.01    4.00   56.03
           O        16.00   20.00  319.98
           Calculated formula weight              974.91
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      1.559
            Test value =      1.500
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.275
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT043_ALERT_1_C Check Reported Molecular Weight ................     989.02
PLAT044_ALERT_1_C Calculated and Reported Dx Differ ..............          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.27
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.36
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       1.56 e/A   
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O2W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....      <O2W'
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.881(10) ......       3.00 su-Ra
              N21  -H21     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.88(3), Rep   0.881(10) ......       3.00 su-Ra
              N51  -H51     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.88(3), Rep   0.881(10) ......       3.00 su-Ra
              N21  -H21     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.88(3), Rep   0.881(10) ......       3.00 su-Ra
              N51  -H51     1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.00(7), Rep   1.990(18) ......       3.89 su-Ra
              H2A  -O11     1.555   7.755
PLAT736_ALERT_1_C H...A   Calc     1.88(5), Rep   1.880(13) ......       3.85 su-Ra
              H4A  -O12     1.555   6.557
PLAT736_ALERT_1_C H...A   Calc     1.93(5), Rep   1.926(17) ......       2.94 su-Ra
              H5A  -O12     1.555   6.567
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C40 H52 Ca2 N4 O20
            Atom count from the _atom_site data:  C40 H38 Ca2 N4 O20
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    4
           From the CIF: _chemical_formula_sum  C40 H52 Ca2 N4 O20
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        160.00    160.00    0.00
           H        208.00    152.00   56.00
           Ca         8.00      8.00    0.00
           N         16.00     16.00    0.00
           O         80.00     80.00    0.00

   2 ALERT level A = In general: serious problem
  10 ALERT level B = Potentially serious problem
  26 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

  23 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and SCHAKAL (Keller, 1999); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

di-µ-aqua-κ⁴O¹:O^1'-bis(µ-2,5-dianilinoterephthalo- κ²O:O')bis[triaquacalcium(I)] tetrahydrate top

Crystal data top

[Ca₂(C₂₀H₂₂N₂O₄)₂(H₂O)₈]·4H₂O	F(000) = 2080
M_r = 989.02	D_x = 1.413 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 25712 reflections
a = 22.4368 (11) Å	θ = 2.8–25.3°
b = 7.1515 (4) Å	µ = 0.33 mm⁻¹
c = 28.9753 (19) Å	T = 173 K
V = 4649.3 (5) Å³	Plate, orange–red
Z = 4	0.23 × 0.17 × 0.09 mm

Data collection top

Stoe IPDS-II two-circle diffractometer	4117 independent reflections
Radiation source: fine-focus sealed tube	3094 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ω scans	θ_max = 25.1°, θ_min = 2.8°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −26→26
T_min = 0.929, T_max = 0.981	k = −7→8
48081 measured reflections	l = −34→34

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)] = 0.098	Hydrogen site location: difmap and geom
wR(F²) = 0.275	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.1038P)² + 27.6871P] where P = (F_o² + 2F_c²)/3
4117 reflections	(Δ/σ)_max < 0.001
332 parameters	Δρ_max = 1.56 e Å⁻³
8 restraints	Δρ_min = −0.66 e Å⁻³

Special details top

Experimental. ;

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	U_iso*/U_eq	Occ. (<1)
Ca1	0.48363 (5)	0.65224 (18)	0.68792 (5)	0.0314 (4)
O1	0.5098 (2)	0.8997 (8)	0.6375 (2)	0.0523 (15)
H1A	0.528 (3)	0.992 (8)	0.649 (3)	0.063*
O2	0.5119 (2)	0.4011 (8)	0.63894 (19)	0.0507 (14)
H2A	0.540 (3)	0.330 (10)	0.646 (2)	0.061*
H2B	0.506 (3)	0.404 (12)	0.6103 (6)	0.061*
O3	0.4027 (2)	0.6450 (8)	0.63004 (18)	0.0469 (13)
O4	0.5000	0.4228 (9)	0.7500	0.0333 (15)
H4A	0.473 (2)	0.345 (7)	0.756 (2)	0.040*
O5	0.5000	0.8869 (9)	0.7500	0.0382 (16)
H5A	0.472 (2)	0.963 (8)	0.754 (3)	0.046*
C1	0.8141 (2)	0.6332 (8)	0.7074 (2)	0.0238 (12)
C2	0.7921 (2)	0.6280 (8)	0.7531 (2)	0.0267 (13)
C3	0.7301 (2)	0.6300 (8)	0.7590 (2)	0.0265 (13)
H3	0.7147	0.6315	0.7896	0.032*
C4	0.6898 (3)	0.6299 (8)	0.7223 (2)	0.0264 (13)
C5	0.7123 (2)	0.6266 (8)	0.6768 (2)	0.0261 (13)
C6	0.7740 (2)	0.6324 (8)	0.6706 (2)	0.0278 (13)
H6	0.7893	0.6359	0.6400	0.033*
C11	0.8797 (2)	0.6426 (8)	0.6961 (2)	0.0272 (13)
O11	0.89580 (17)	0.6403 (7)	0.65469 (15)	0.0334 (10)
O12	0.91703 (17)	0.6588 (6)	0.72935 (15)	0.0299 (10)
N21	0.8308 (2)	0.6396 (9)	0.79079 (18)	0.0351 (13)
H21	0.8686 (10)	0.660 (10)	0.785 (2)	0.038 (19)*
C21	0.8246 (3)	0.5801 (9)	0.8362 (2)	0.0294 (14)
C22	0.8687 (3)	0.6368 (10)	0.8673 (2)	0.0366 (15)
H22	0.9001	0.7148	0.8569	0.044*
C23	0.8672 (3)	0.5813 (10)	0.9130 (2)	0.0399 (16)
H23	0.8975	0.6223	0.9336	0.048*
C24	0.8218 (3)	0.4657 (11)	0.9289 (2)	0.0426 (17)
H24	0.8208	0.4276	0.9603	0.051*
C25	0.7783 (3)	0.4070 (10)	0.8987 (2)	0.0406 (17)
H25	0.7474	0.3276	0.9095	0.049*
C26	0.7789 (3)	0.4624 (9)	0.8524 (2)	0.0312 (14)
H26	0.7486	0.4207	0.8319	0.037*
C41	0.6246 (3)	0.6420 (9)	0.7342 (2)	0.0311 (14)
O41	0.60978 (18)	0.6366 (7)	0.77551 (16)	0.0389 (11)
O42	0.58738 (17)	0.6606 (7)	0.70134 (16)	0.0368 (11)
N51	0.6731 (2)	0.6308 (9)	0.63955 (19)	0.0365 (13)
H51	0.6360 (11)	0.629 (10)	0.649 (2)	0.04 (2)*
C51	0.6810 (3)	0.5766 (9)	0.5935 (2)	0.0309 (14)
C52	0.7276 (3)	0.4702 (9)	0.5762 (2)	0.0289 (14)
H52	0.7582	0.4288	0.5965	0.035*
C53	0.7303 (3)	0.4233 (10)	0.5297 (2)	0.0358 (15)
H53	0.7626	0.3501	0.5187	0.043*
C54	0.6867 (3)	0.4817 (11)	0.4994 (3)	0.0408 (17)
H54	0.6891	0.4513	0.4675	0.049*
C55	0.6386 (3)	0.5869 (11)	0.5165 (2)	0.0434 (18)
H55	0.6078	0.6259	0.4962	0.052*
C56	0.6358 (3)	0.6337 (10)	0.5624 (2)	0.0386 (16)
H56	0.6031	0.7052	0.5735	0.046*
O1W	0.8811 (2)	0.6323 (8)	0.55965 (19)	0.0571 (15)
O2W	0.5075 (4)	0.3421 (18)	0.5349 (4)	0.085 (4)	0.658 (14)
O2W'	0.9804 (7)	0.452 (3)	0.5342 (5)	0.069 (7)	0.342 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.0162 (6)	0.0278 (7)	0.0502 (8)	0.0026 (5)	0.0044 (5)	0.0012 (6)
O1	0.036 (3)	0.049 (3)	0.072 (4)	−0.017 (2)	−0.014 (3)	0.020 (3)
O2	0.042 (3)	0.052 (3)	0.058 (3)	0.021 (2)	−0.002 (3)	−0.005 (3)
O3	0.035 (3)	0.049 (3)	0.056 (3)	−0.002 (2)	−0.007 (2)	0.004 (3)
O4	0.017 (3)	0.027 (3)	0.055 (4)	0.000	0.010 (3)	0.000
O5	0.022 (3)	0.022 (3)	0.071 (5)	0.000	0.015 (3)	0.000
C1	0.018 (3)	0.018 (3)	0.036 (3)	−0.004 (2)	0.000 (2)	0.005 (2)
C2	0.017 (3)	0.022 (3)	0.041 (3)	−0.003 (2)	0.001 (2)	0.000 (3)
C3	0.018 (3)	0.025 (3)	0.037 (3)	−0.003 (2)	0.001 (2)	−0.001 (3)
C4	0.020 (3)	0.018 (3)	0.041 (3)	0.002 (2)	0.003 (2)	−0.004 (3)
C5	0.016 (3)	0.024 (3)	0.039 (3)	0.004 (2)	0.000 (2)	−0.004 (3)
C6	0.018 (3)	0.024 (3)	0.041 (3)	0.008 (2)	0.001 (2)	0.001 (3)
C11	0.020 (3)	0.018 (3)	0.044 (4)	0.001 (2)	0.001 (3)	0.003 (3)
O11	0.0168 (19)	0.044 (3)	0.039 (2)	−0.0033 (19)	0.0022 (18)	0.001 (2)
O12	0.0166 (19)	0.029 (2)	0.044 (2)	−0.0018 (18)	−0.0027 (17)	0.000 (2)
N21	0.018 (3)	0.052 (4)	0.035 (3)	−0.008 (3)	0.001 (2)	0.006 (3)
C21	0.028 (3)	0.027 (3)	0.033 (3)	0.002 (3)	0.001 (3)	0.001 (3)
C22	0.025 (3)	0.043 (4)	0.043 (4)	−0.004 (3)	0.001 (3)	−0.003 (3)
C23	0.043 (4)	0.044 (4)	0.032 (4)	0.003 (3)	−0.002 (3)	−0.008 (3)
C24	0.047 (4)	0.048 (4)	0.033 (4)	0.010 (4)	0.005 (3)	0.005 (3)
C25	0.042 (4)	0.032 (4)	0.047 (4)	0.001 (3)	0.007 (3)	0.001 (3)
C26	0.027 (3)	0.031 (3)	0.036 (3)	0.002 (3)	0.004 (3)	−0.002 (3)
C41	0.018 (3)	0.024 (3)	0.052 (4)	0.003 (2)	0.005 (3)	−0.005 (3)
O41	0.019 (2)	0.052 (3)	0.045 (3)	−0.003 (2)	0.0076 (19)	−0.003 (2)
O42	0.015 (2)	0.045 (3)	0.051 (3)	0.006 (2)	0.0030 (19)	0.003 (2)
N51	0.013 (2)	0.057 (4)	0.039 (3)	0.003 (2)	0.000 (2)	−0.006 (3)
C51	0.018 (3)	0.039 (4)	0.035 (3)	−0.008 (3)	0.000 (2)	0.006 (3)
C52	0.018 (3)	0.030 (3)	0.039 (4)	−0.001 (2)	−0.001 (2)	0.003 (3)
C53	0.026 (3)	0.038 (4)	0.043 (4)	−0.007 (3)	0.003 (3)	−0.005 (3)
C54	0.032 (3)	0.048 (4)	0.042 (4)	−0.010 (3)	0.001 (3)	−0.003 (3)
C55	0.033 (4)	0.054 (5)	0.044 (4)	−0.006 (3)	−0.009 (3)	0.006 (4)
C56	0.019 (3)	0.048 (4)	0.049 (4)	−0.001 (3)	−0.003 (3)	−0.001 (3)
O1W	0.051 (3)	0.061 (4)	0.060 (3)	0.016 (3)	−0.005 (3)	−0.008 (3)
O2W	0.039 (5)	0.127 (10)	0.088 (8)	−0.022 (6)	−0.029 (5)	0.046 (7)
O2W'	0.030 (8)	0.132 (18)	0.045 (10)	0.006 (10)	0.014 (7)	0.017 (10)

Geometric parameters (Å, º) top

Ca1—O41ⁱ	2.351 (4)	N21—C21	1.390 (8)
Ca1—O42	2.361 (4)	N21—H21	0.881 (10)
Ca1—O1	2.368 (5)	C21—C22	1.398 (9)
Ca1—O2	2.375 (5)	C21—C26	1.406 (9)
Ca1—O4	2.463 (4)	C22—C23	1.382 (9)
Ca1—O3	2.472 (5)	C22—H22	0.9500
Ca1—O5	2.487 (4)	C23—C24	1.390 (10)
Ca1—Ca1ⁱ	3.672 (3)	C23—H23	0.9500
O1—H1A	0.839 (11)	C24—C25	1.376 (10)
O2—H2A	0.842 (10)	C24—H24	0.9500
O2—H2B	0.840 (10)	C25—C26	1.400 (9)
O4—Ca1ⁱ	2.463 (4)	C25—H25	0.9500
O4—H4A	0.840 (10)	C26—H26	0.9500
O5—Ca1ⁱ	2.487 (4)	C41—O41	1.241 (8)
O5—H5A	0.840 (10)	C41—O42	1.274 (8)
C1—C6	1.398 (8)	O41—Ca1ⁱ	2.351 (4)
C1—C2	1.412 (8)	N51—C51	1.400 (8)
C1—C11	1.508 (8)	N51—H51	0.881 (10)
C2—N21	1.399 (8)	C51—C52	1.387 (9)
C2—C3	1.401 (8)	C51—C56	1.417 (9)
C3—C4	1.396 (8)	C52—C53	1.389 (9)
C3—H3	0.9500	C52—H52	0.9500
C4—C5	1.412 (9)	C53—C54	1.382 (10)
C4—C41	1.508 (8)	C53—H53	0.9500
C5—N51	1.392 (8)	C54—C55	1.407 (10)
C5—C6	1.398 (8)	C54—H54	0.9500
C6—H6	0.9500	C55—C56	1.373 (10)
C11—O11	1.254 (7)	C55—H55	0.9500
C11—O12	1.282 (7)	C56—H56	0.9500

O41ⁱ—Ca1—O42	143.70 (17)	C5—C6—C1	122.7 (6)
O41ⁱ—Ca1—O1	122.32 (19)	C5—C6—H6	118.7
O42—Ca1—O1	80.66 (17)	C1—C6—H6	118.7
O41ⁱ—Ca1—O2	118.1 (2)	O11—C11—O12	122.1 (5)
O42—Ca1—O2	81.62 (18)	O11—C11—C1	119.3 (5)
O1—Ca1—O2	97.5 (2)	O12—C11—C1	118.5 (5)
O41ⁱ—Ca1—O4	76.82 (12)	C21—N21—C2	131.2 (5)
O42—Ca1—O4	75.50 (12)	C21—N21—H21	110 (4)
O1—Ca1—O4	155.67 (14)	C2—N21—H21	117 (4)
O2—Ca1—O4	83.84 (18)	N21—C21—C22	116.8 (6)
O41ⁱ—Ca1—O3	69.52 (17)	N21—C21—C26	124.9 (6)
O42—Ca1—O3	146.76 (17)	C22—C21—C26	118.3 (6)
O1—Ca1—O3	77.29 (17)	C23—C22—C21	121.2 (6)
O2—Ca1—O3	76.99 (18)	C23—C22—H22	119.4
O4—Ca1—O3	126.23 (15)	C21—C22—H22	119.4
O41ⁱ—Ca1—O5	80.66 (13)	C22—C23—C24	120.3 (7)
O42—Ca1—O5	73.63 (13)	C22—C23—H23	119.9
O1—Ca1—O5	84.54 (18)	C24—C23—H23	119.9
O2—Ca1—O5	154.52 (15)	C25—C24—C23	119.4 (6)
O4—Ca1—O5	84.22 (16)	C25—C24—H24	120.3
O3—Ca1—O5	127.82 (15)	C23—C24—H24	120.3
O41ⁱ—Ca1—Ca1ⁱ	74.73 (12)	C24—C25—C26	121.1 (7)
O42—Ca1—Ca1ⁱ	68.98 (12)	C24—C25—H25	119.5
O1—Ca1—Ca1ⁱ	123.66 (14)	C26—C25—H25	119.5
O2—Ca1—Ca1ⁱ	122.14 (14)	C25—C26—C21	119.7 (6)
O4—Ca1—Ca1ⁱ	41.79 (12)	C25—C26—H26	120.2
O3—Ca1—Ca1ⁱ	144.25 (13)	C21—C26—H26	120.2
O5—Ca1—Ca1ⁱ	42.43 (11)	O41—C41—O42	123.3 (5)
Ca1—O1—H1A	118 (6)	O41—C41—C4	118.6 (6)
Ca1—O2—H2A	120 (5)	O42—C41—C4	118.1 (6)
Ca1—O2—H2B	122 (5)	C41—O41—Ca1ⁱ	132.1 (4)
H2A—O2—H2B	113 (4)	C41—O42—Ca1	140.0 (4)
Ca1—O4—Ca1ⁱ	96.4 (2)	C5—N51—C51	130.6 (5)
Ca1—O4—H4A	118 (5)	C5—N51—H51	110 (5)
Ca1ⁱ—O4—H4A	114 (5)	C51—N51—H51	115 (5)
Ca1—O5—Ca1ⁱ	95.1 (2)	C52—C51—N51	126.3 (6)
Ca1—O5—H5A	115 (5)	C52—C51—C56	117.9 (6)
Ca1ⁱ—O5—H5A	116 (5)	N51—C51—C56	115.7 (6)
C6—C1—C2	119.3 (5)	C51—C52—C53	121.1 (6)
C6—C1—C11	117.5 (5)	C51—C52—H52	119.5
C2—C1—C11	123.2 (5)	C53—C52—H52	119.5
N21—C2—C3	121.3 (6)	C54—C53—C52	120.9 (6)
N21—C2—C1	120.8 (5)	C54—C53—H53	119.5
C3—C2—C1	117.6 (6)	C52—C53—H53	119.5
C4—C3—C2	123.2 (6)	C53—C54—C55	118.7 (7)
C4—C3—H3	118.4	C53—C54—H54	120.7
C2—C3—H3	118.4	C55—C54—H54	120.7
C3—C4—C5	118.8 (5)	C56—C55—C54	120.6 (7)
C3—C4—C41	116.9 (6)	C56—C55—H55	119.7
C5—C4—C41	124.2 (6)	C54—C55—H55	119.7
N51—C5—C6	121.8 (6)	C55—C56—C51	120.8 (6)
N51—C5—C4	119.9 (5)	C55—C56—H56	119.6
C6—C5—C4	118.2 (6)	C51—C56—H56	119.6

O41ⁱ—Ca1—O4—Ca1ⁱ	−81.73 (13)	N21—C21—C22—C23	−178.4 (6)
O42—Ca1—O4—Ca1ⁱ	74.55 (13)	C26—C21—C22—C23	−0.9 (10)
O1—Ca1—O4—Ca1ⁱ	62.9 (5)	C21—C22—C23—C24	0.6 (11)
O2—Ca1—O4—Ca1ⁱ	157.45 (14)	C22—C23—C24—C25	0.0 (11)
O3—Ca1—O4—Ca1ⁱ	−133.63 (18)	C23—C24—C25—C26	−0.3 (11)
O5—Ca1—O4—Ca1ⁱ	0.0	C24—C25—C26—C21	−0.1 (10)
O41ⁱ—Ca1—O5—Ca1ⁱ	77.55 (12)	N21—C21—C26—C25	178.0 (6)
O42—Ca1—O5—Ca1ⁱ	−76.55 (13)	C22—C21—C26—C25	0.7 (9)
O1—Ca1—O5—Ca1ⁱ	−158.39 (14)	C3—C4—C41—O41	−5.5 (9)
O2—Ca1—O5—Ca1ⁱ	−62.4 (4)	C5—C4—C41—O41	177.3 (6)
O4—Ca1—O5—Ca1ⁱ	0.001 (1)	C3—C4—C41—O42	173.2 (6)
O3—Ca1—O5—Ca1ⁱ	132.34 (18)	C5—C4—C41—O42	−4.0 (9)
C6—C1—C2—N21	−176.3 (6)	O42—C41—O41—Ca1ⁱ	0.7 (10)
C11—C1—C2—N21	2.8 (9)	C4—C41—O41—Ca1ⁱ	179.4 (4)
C6—C1—C2—C3	−2.6 (9)	O41—C41—O42—Ca1	−11.3 (11)
C11—C1—C2—C3	176.5 (5)	C4—C41—O42—Ca1	170.0 (4)
N21—C2—C3—C4	176.1 (6)	O41ⁱ—Ca1—O42—C41	8.5 (8)
C1—C2—C3—C4	2.4 (9)	O1—Ca1—O42—C41	142.3 (7)
C2—C3—C4—C5	0.4 (9)	O2—Ca1—O42—C41	−118.7 (7)
C2—C3—C4—C41	−177.0 (6)	O4—Ca1—O42—C41	−32.9 (7)
C3—C4—C5—N51	−178.5 (6)	O3—Ca1—O42—C41	−168.9 (6)
C41—C4—C5—N51	−1.4 (9)	O5—Ca1—O42—C41	55.2 (7)
C3—C4—C5—C6	−2.9 (9)	Ca1ⁱ—Ca1—O42—C41	10.6 (6)
C41—C4—C5—C6	174.3 (6)	C6—C5—N51—C51	25.3 (11)
N51—C5—C6—C1	178.3 (6)	C4—C5—N51—C51	−159.3 (7)
C4—C5—C6—C1	2.8 (9)	C5—N51—C51—C52	13.7 (11)
C2—C1—C6—C5	0.0 (9)	C5—N51—C51—C56	−167.9 (7)
C11—C1—C6—C5	−179.1 (6)	N51—C51—C52—C53	179.2 (6)
C6—C1—C11—O11	−3.4 (8)	C56—C51—C52—C53	0.9 (9)
C2—C1—C11—O11	177.5 (6)	C51—C52—C53—C54	0.1 (10)
C6—C1—C11—O12	174.4 (5)	C52—C53—C54—C55	−1.2 (10)
C2—C1—C11—O12	−4.6 (9)	C53—C54—C55—C56	1.3 (11)
C3—C2—N21—C21	30.1 (11)	C54—C55—C56—C51	−0.2 (11)
C1—C2—N21—C21	−156.5 (7)	C52—C51—C56—C55	−0.9 (10)
C2—N21—C21—C22	−171.2 (7)	N51—C51—C56—C55	−179.4 (6)
C2—N21—C21—C26	11.5 (11)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O11ⁱⁱ	0.84 (1)	2.02 (5)	2.773 (6)	149 (8)
O2—H2A···O11ⁱⁱⁱ	0.84 (1)	1.99 (2)	2.824 (6)	171 (7)
O2—H2B···O2W	0.84 (1)	2.23 (3)	3.045 (12)	163 (7)
O4—H4A···O12^iv	0.84 (1)	1.88 (1)	2.718 (6)	175 (7)
O5—H5A···O12^v	0.84 (1)	1.93 (2)	2.758 (6)	170 (7)
N21—H21···O12	0.88 (1)	1.93 (5)	2.633 (6)	135 (6)
N51—H51···O42	0.88 (1)	1.87 (4)	2.635 (6)	144 (6)

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

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Calcium anilate hexa­hydrate

Supporting information

Key indicators

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Calcium anilate hexahydrate