1,10-Phenanthroline (2R,3R)-tartaric acid trihydrate

In the title compound, C₁₂H₈N₂·C₄H₆O₆·3H₂O, the mol­ecules are linked by strong O—H...O hydrogen bonds and π–π inter­actions, generating an infinite three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.053
• wR factor = 0.140
• Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H6     ..  H71     ..       1.60 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.34
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.36
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT731_ALERT_1_C Bond    Calc     0.82(5), Rep     0.82(2) ......       2.50 su-Rat
              O3   -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(4), Rep   0.870(19) ......       2.11 su-Rat
              O9   -H92     1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               2011
           Count of symmetry unique reflns         2018
           Completeness (_total/calc)             99.65%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1,10-phenanthroline–(L)-(+)-tartaric acid–water (1/1/3)

Crystal data

C12H8N2·C4H6O6·3H2O	F(000) = 808
Mr = 384.34	Dx = 1.436 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1518 reflections
a = 7.1625 (11) Å	θ = 2.6–22.2°
b = 12.680 (2) Å	µ = 0.12 mm^−1
c = 19.573 (5) Å	T = 293 K
V = 1777.6 (6) Å^3	Block, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2011 independent reflections
Radiation source: fine-focus sealed tube	1607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.053
ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.965, Tmax = 0.977	k = −14→15
7952 measured reflections	l = −11→24

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0766P)^2 + 0.2889P] where P = (Fo^2 + 2Fc^2)/3
2011 reflections	(Δ/σ)max < 0.001
274 parameters	Δρmax = 0.35 e Å^−3
13 restraints	Δρmin = −0.23 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9452 (8)	0.4536 (4)	0.4662 (2)	0.0661 (13)
H1A	0.9479	0.5078	0.4341	0.079*
C2	0.9442 (9)	0.4779 (5)	0.5354 (3)	0.0759 (16)
H2A	0.9417	0.5478	0.5499	0.091*
C3	0.9468 (8)	0.3989 (5)	0.5812 (2)	0.0711 (15)
H3A	0.9489	0.4146	0.6276	0.085*
C4	0.9464 (7)	0.2919 (4)	0.55991 (19)	0.0573 (12)
C5	0.9474 (9)	0.2019 (5)	0.6053 (2)	0.0748 (16)
H5A	0.9512	0.2132	0.6523	0.090*
C6	0.9432 (9)	0.1049 (5)	0.5824 (2)	0.0729 (15)
H6A	0.9440	0.0494	0.6134	0.088*
C7	0.9371 (7)	0.0819 (4)	0.51048 (19)	0.0534 (11)
C8	0.9305 (7)	−0.0203 (4)	0.4835 (2)	0.0609 (12)
H8A	0.9293	−0.0783	0.5126	0.073*
C9	0.9260 (7)	−0.0344 (4)	0.4151 (2)	0.0585 (12)
H9A	0.9190	−0.1019	0.3966	0.070*
C10	0.9320 (7)	0.0541 (3)	0.3726 (2)	0.0538 (11)
H10A	0.9301	0.0434	0.3256	0.065*
C11	0.9403 (6)	0.1668 (3)	0.46375 (17)	0.0431 (9)
C12	0.9435 (6)	0.2724 (3)	0.48962 (18)	0.0448 (10)
N1	0.9402 (6)	0.1519 (3)	0.39513 (15)	0.0489 (9)
N2	0.9423 (6)	0.3549 (3)	0.44526 (16)	0.0482 (9)
C13	0.4354 (5)	0.7462 (3)	0.34306 (17)	0.0407 (9)
C14	0.2251 (5)	0.7480 (3)	0.34342 (17)	0.0341 (8)
H14A	0.1835	0.8191	0.3312	0.041*
C15	0.1454 (5)	0.6705 (3)	0.29162 (17)	0.0321 (8)
H15A	0.1875	0.6911	0.2459	0.039*
C16	−0.0690 (5)	0.6725 (3)	0.29308 (15)	0.0298 (7)
O1	0.5233 (5)	0.7205 (5)	0.39333 (15)	0.1003 (17)
O2	0.5130 (3)	0.7725 (2)	0.28563 (13)	0.0417 (7)
H2	0.623 (3)	0.758 (4)	0.291 (2)	0.062*
O3	0.1543 (4)	0.7233 (3)	0.40861 (12)	0.0522 (8)
H3	0.221 (7)	0.749 (4)	0.438 (2)	0.078*
O4	0.2043 (4)	0.5661 (2)	0.30431 (15)	0.0478 (7)
H4	0.306 (4)	0.553 (4)	0.285 (2)	0.072*
O5	−0.1543 (4)	0.5913 (2)	0.30408 (17)	0.0550 (8)
O6	−0.1415 (3)	0.7618 (2)	0.28281 (14)	0.0398 (6)
H6	−0.105 (6)	0.794 (3)	0.2501 (16)	0.060*
O7	0.9307 (5)	0.3803 (2)	0.31070 (15)	0.0519 (8)
H71	1.046 (3)	0.369 (4)	0.312 (2)	0.078*
H72	0.917 (7)	0.4470 (18)	0.316 (3)	0.078*
O8	0.8169 (5)	0.7045 (3)	0.47615 (13)	0.0639 (9)
H81	0.908 (5)	0.710 (6)	0.450 (2)	0.096*
H82	0.722 (5)	0.711 (5)	0.449 (2)	0.096*
O9	0.5312 (4)	0.5047 (2)	0.24350 (16)	0.0562 (8)
H91	0.574 (7)	0.442 (2)	0.240 (3)	0.084*
H92	0.612 (6)	0.533 (3)	0.271 (2)	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.084 (4)	0.051 (3)	0.063 (3)	0.008 (3)	−0.001 (3)	−0.008 (2)
C2	0.088 (4)	0.070 (4)	0.070 (3)	0.016 (4)	−0.012 (3)	−0.027 (3)
C3	0.062 (3)	0.105 (4)	0.047 (2)	0.000 (4)	−0.002 (3)	−0.023 (3)
C4	0.050 (3)	0.085 (3)	0.0362 (19)	0.002 (3)	0.003 (2)	−0.014 (2)
C5	0.085 (4)	0.111 (5)	0.0279 (19)	−0.004 (4)	−0.001 (2)	0.005 (2)
C6	0.099 (4)	0.080 (4)	0.040 (2)	−0.005 (4)	−0.002 (3)	0.020 (2)
C7	0.052 (3)	0.066 (3)	0.042 (2)	−0.002 (3)	0.001 (2)	0.014 (2)
C8	0.064 (3)	0.053 (3)	0.066 (3)	0.002 (3)	−0.002 (3)	0.020 (2)
C9	0.066 (3)	0.046 (3)	0.064 (3)	0.006 (2)	0.002 (3)	0.004 (2)
C10	0.068 (3)	0.047 (3)	0.046 (2)	0.012 (3)	0.000 (2)	−0.0003 (18)
C11	0.042 (2)	0.051 (2)	0.0359 (18)	0.003 (2)	0.0012 (17)	0.0043 (17)
C12	0.037 (2)	0.060 (3)	0.0373 (18)	0.000 (2)	−0.0011 (17)	−0.0002 (18)
N1	0.063 (2)	0.049 (2)	0.0348 (15)	0.010 (2)	0.0032 (17)	0.0029 (14)
N2	0.056 (2)	0.042 (2)	0.0469 (18)	0.0049 (19)	0.0022 (18)	−0.0032 (15)
C13	0.0248 (17)	0.061 (3)	0.0366 (17)	−0.001 (2)	−0.0006 (15)	−0.0048 (18)
C14	0.0265 (17)	0.044 (2)	0.0323 (16)	0.0002 (16)	0.0013 (13)	−0.0032 (16)
C15	0.0230 (16)	0.037 (2)	0.0368 (17)	0.0021 (16)	0.0023 (14)	0.0030 (16)
C16	0.0223 (16)	0.039 (2)	0.0280 (15)	0.0008 (17)	0.0008 (13)	0.0002 (15)
O1	0.0378 (18)	0.225 (6)	0.0378 (15)	0.010 (3)	−0.0049 (13)	0.016 (2)
O2	0.0245 (12)	0.0544 (17)	0.0460 (13)	0.0017 (12)	0.0001 (11)	0.0124 (13)
O3	0.0312 (14)	0.092 (2)	0.0328 (12)	−0.0056 (17)	0.0042 (11)	−0.0104 (14)
O4	0.0398 (16)	0.0391 (16)	0.0644 (18)	0.0113 (14)	0.0029 (13)	0.0039 (13)
O5	0.0329 (14)	0.0385 (16)	0.094 (2)	−0.0082 (13)	−0.0017 (16)	0.0106 (15)
O6	0.0244 (12)	0.0404 (16)	0.0544 (15)	−0.0008 (12)	0.0028 (11)	0.0118 (12)
O7	0.0624 (19)	0.0378 (16)	0.0555 (15)	0.0011 (16)	0.0064 (16)	−0.0011 (13)
O8	0.0426 (18)	0.112 (3)	0.0373 (14)	−0.001 (2)	0.0030 (13)	−0.0044 (17)
O9	0.0494 (18)	0.0523 (19)	0.0668 (19)	0.0030 (16)	−0.0055 (16)	−0.0052 (15)

Geometric parameters (Å, º)

C1—N2	1.317 (6)	C12—N2	1.359 (5)
C1—C2	1.391 (7)	C13—O1	1.212 (5)
C1—H1A	0.9300	C13—O2	1.298 (4)
C2—C3	1.344 (8)	C13—C14	1.507 (5)
C2—H2A	0.9300	C14—O3	1.408 (4)
C3—C4	1.419 (8)	C14—C15	1.523 (5)
C3—H3A	0.9300	C14—H14A	0.9800
C4—C12	1.398 (5)	C15—O4	1.411 (5)
C4—C5	1.447 (8)	C15—C16	1.536 (5)
C5—C6	1.310 (8)	C15—H15A	0.9800
C5—H5A	0.9300	C16—O5	1.217 (4)
C6—C7	1.438 (6)	C16—O6	1.263 (4)
C6—H6A	0.9300	O2—H2	0.82 (2)
C7—C8	1.400 (7)	O3—H3	0.82 (2)
C7—C11	1.413 (6)	O4—H4	0.84 (2)
C8—C9	1.350 (6)	O6—H6	0.80 (2)
C8—H8A	0.9300	O7—H71	0.84 (2)
C9—C10	1.398 (6)	O7—H72	0.858 (19)
C9—H9A	0.9300	O8—H81	0.83 (2)
C10—N1	1.317 (6)	O8—H82	0.87 (2)
C10—H10A	0.9300	O9—H91	0.86 (2)
C11—N1	1.356 (5)	O9—H92	0.870 (19)
C11—C12	1.432 (6)
N2—C1—C2	120.9 (5)	C7—C11—C12	119.0 (3)
N2—C1—H1A	119.6	N2—C12—C4	119.5 (4)
C2—C1—H1A	119.6	N2—C12—C11	119.6 (3)
C3—C2—C1	119.0 (5)	C4—C12—C11	120.9 (4)
C3—C2—H2A	120.5	C10—N1—C11	117.5 (4)
C1—C2—H2A	120.5	C1—N2—C12	122.2 (4)
C2—C3—C4	121.1 (4)	O1—C13—O2	123.4 (3)
C2—C3—H3A	119.4	O1—C13—C14	121.3 (3)
C4—C3—H3A	119.4	O2—C13—C14	115.3 (3)
C12—C4—C3	117.3 (4)	O3—C14—C13	111.1 (3)
C12—C4—C5	117.7 (4)	O3—C14—C15	108.9 (3)
C3—C4—C5	125.0 (4)	C13—C14—C15	111.2 (3)
C6—C5—C4	122.0 (4)	O3—C14—H14A	108.5
C6—C5—H5A	119.0	C13—C14—H14A	108.5
C4—C5—H5A	119.0	C15—C14—H14A	108.5
C5—C6—C7	121.8 (4)	O4—C15—C14	112.1 (3)
C5—C6—H6A	119.1	O4—C15—C16	108.1 (3)
C7—C6—H6A	119.1	C14—C15—C16	110.6 (3)
C8—C7—C11	117.5 (4)	O4—C15—H15A	108.7
C8—C7—C6	123.9 (4)	C14—C15—H15A	108.7
C11—C7—C6	118.6 (4)	C16—C15—H15A	108.7
C9—C8—C7	119.8 (4)	O5—C16—O6	125.5 (3)
C9—C8—H8A	120.1	O5—C16—C15	119.5 (3)
C7—C8—H8A	120.1	O6—C16—C15	115.0 (3)
C8—C9—C10	118.8 (4)	C13—O2—H2	104 (3)
C8—C9—H9A	120.6	C14—O3—H3	110 (4)
C10—C9—H9A	120.6	C15—O4—H4	111 (4)
N1—C10—C9	123.9 (4)	C16—O6—H6	117 (3)
N1—C10—H10A	118.0	H71—O7—H72	106 (3)
C9—C10—H10A	118.0	H81—O8—H82	104 (3)
N1—C11—C7	122.3 (4)	H91—O9—H92	101 (3)
N1—C11—C12	118.7 (3)
N2—C1—C2—C3	2.3 (10)	C7—C11—C12—N2	−178.5 (4)
C1—C2—C3—C4	−1.4 (10)	N1—C11—C12—C4	−179.1 (4)
C2—C3—C4—C12	0.1 (8)	C7—C11—C12—C4	1.0 (6)
C2—C3—C4—C5	−179.4 (6)	C9—C10—N1—C11	−0.9 (8)
C12—C4—C5—C6	−0.9 (9)	C7—C11—N1—C10	1.8 (7)
C3—C4—C5—C6	178.6 (6)	C12—C11—N1—C10	−178.2 (4)
C4—C5—C6—C7	0.0 (11)	C2—C1—N2—C12	−1.9 (9)
C5—C6—C7—C8	−179.3 (6)	C4—C12—N2—C1	0.5 (7)
C5—C6—C7—C11	1.5 (9)	C11—C12—N2—C1	−180.0 (5)
C11—C7—C8—C9	−0.5 (8)	O1—C13—C14—O3	3.6 (7)
C6—C7—C8—C9	−179.7 (5)	O2—C13—C14—O3	−177.2 (3)
C7—C8—C9—C10	1.3 (9)	O1—C13—C14—C15	−118.0 (5)
C8—C9—C10—N1	−0.7 (9)	O2—C13—C14—C15	61.3 (5)
C8—C7—C11—N1	−1.1 (7)	O3—C14—C15—O4	−64.1 (4)
C6—C7—C11—N1	178.2 (5)	C13—C14—C15—O4	58.7 (4)
C8—C7—C11—C12	178.8 (4)	O3—C14—C15—C16	56.6 (4)
C6—C7—C11—C12	−1.9 (7)	C13—C14—C15—C16	179.4 (3)
C3—C4—C12—N2	0.4 (7)	O4—C15—C16—O5	0.1 (5)
C5—C4—C12—N2	179.9 (5)	C14—C15—C16—O5	−123.0 (4)
C3—C4—C12—C11	−179.1 (5)	O4—C15—C16—O6	179.6 (3)
C5—C4—C12—C11	0.4 (7)	C14—C15—C16—O6	56.5 (4)
N1—C11—C12—N2	1.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O9	0.84 (3)	1.91 (3)	2.740 (4)	173 (5)
O8—H82···O1	0.87 (4)	1.80 (4)	2.663 (5)	178 (6)
O2—H2···O6^i	0.82 (2)	1.70 (2)	2.479 (3)	161 (4)
O3—H3···O8^ii	0.82 (4)	1.91 (4)	2.699 (4)	163 (5)
O6—H6···O7^iii	0.80 (3)	2.04 (4)	2.808 (4)	159 (4)
O7—H72···O4^i	0.86 (2)	2.56 (4)	3.067 (4)	119 (4)
O7—H72···O5^i	0.86 (2)	1.91 (3)	2.747 (4)	163 (6)
O7—H71···O6^iv	0.84 (2)	2.41 (4)	2.808 (4)	110 (3)
O8—H81···O3^i	0.83 (4)	1.95 (4)	2.765 (4)	167 (4)
O9—H91···O2^iv	0.86 (3)	2.29 (3)	3.016 (5)	142 (4)
O9—H92···O5^i	0.88 (4)	1.94 (4)	2.772 (4)	159 (4)

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