Cinchonidinium (R,R)-tartrate monohydrate

Two symmetry-related cinchonidinium ions of the title compound, C₁₉H₂₃N₂O⁺·0.5C₄H₄O₆^2-·H₂O, are linked through hydrogen bonds, with a tartrate ion positioned on the twofold axis.

Key indicators

• Single-crystal X-ray study
• T = 122 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.000
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level A
REFI005_ALERT_1_A  _refine_ls_wR_factor_ref is missing
            R factor of coefficient for refinement reflections.
            The following tests will not be performed
            RFACR_01
PLAT027_ALERT_3_A _diffrn_reflns_theta_full too Low ..............       0.00 Deg.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.00
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?
PLAT037_ALERT_1_A _diffrn_reflns_theta_full .......... Not Given .          ?
PLAT038_ALERT_1_A _diffrn_measured_fraction_theta_max  Not Given .          ?
PLAT039_ALERT_1_A _diffrn_measured_fraction_theta_full Not Given .          ?
PLAT761_ALERT_1_A CIF Contains no X-H Bonds ......................          ?
PLAT762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles ..........          ?

Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.21 Ratio
PLAT417_ALERT_2_B Short Inter D-H..H-D       HO18   ..  HW1B     =       2.05 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.12 Ratio
PLAT353_ALERT_3_C Long    N-H Bond (0.87A)   N2     -   HN2      =       1.03 Ang.
PLAT417_ALERT_2_C Short Inter D-H..H-D       HO18   ..  HW1A     =       2.10 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

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           74.89
           From the CIF: _reflns_number_total               3940
           Count of symmetry unique reflns         2157
           Completeness (_total/calc)            182.66%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1783
           Fraction of Friedel pairs measured     0.827
           Are heavy atom types Z>Si present           no

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

   8 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
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: DREADD (Blessing 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: Please provide.

Cinchonidinium (R,R)-tartrate monohydrate

Crystal data

C19H23N2O^+·0.5C4H4O6^2^−·H2O	F(000) = 828
Mr = 387.45	Dx = 1.337 Mg m^−3
Monoclinic, C2	Cu Kα radiation, λ = 1.54180 Å
a = 19.972 (3) Å	Cell parameters from 20 reflections
b = 6.509 (3) Å	θ = 41.4–42.6°
c = 15.472 (3) Å	µ = 0.78 mm^−1
β = 106.874 (13)°	T = 122 K
V = 1924.6 (10) Å^3	Rod, colourless
Z = 4	0.35 × 0.1 × 0.1 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: fine-focus sealed tube	θmax = 74.9°, θmin = 3.0°
Graphite monochromator	h = −24→23
ω–2θ scans	k = −8→8
3940 measured reflections	l = −19→19
3940 independent reflections	5 standard reflections every 167 min
3841 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.029	All H-atom parameters refined
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0465P)^2 + 0.5369P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = −0.001
3940 reflections	Δρmax = 0.15 e Å^−3
361 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: (Flack, 1983), 0000 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.13 (12)

Special details

Experimental. 'none'

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 on F² for ALL reflections except for 0 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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	0.40463 (6)	0.3420 (2)	−0.00111 (8)	0.0168 (2)
O1	0.36798 (4)	0.19686 (14)	−0.04606 (6)	0.0212 (2)
O2	0.38253 (5)	0.5148 (2)	0.01074 (6)	0.0234 (2)
C2	0.48328 (6)	0.3019 (2)	0.03907 (8)	0.0160 (2)
H2	0.4910 (8)	0.166 (3)	0.0714 (11)	0.021 (4)*
O3	0.51430 (5)	0.4535 (2)	0.10391 (6)	0.0233 (2)
HO3	0.4882 (12)	0.549 (4)	0.0949 (16)	0.051 (7)*
C9	0.32208 (6)	0.4950 (2)	0.67074 (8)	0.0182 (2)
C10	0.35884 (6)	0.3236 (2)	0.64901 (8)	0.0207 (3)
C11	0.38840 (6)	0.1636 (2)	0.71034 (9)	0.0236 (3)
H11	0.3837 (10)	0.170 (3)	0.7723 (13)	0.041 (5)*
C12	0.42210 (7)	0.0015 (3)	0.68458 (11)	0.0303 (3)
H12	0.4416 (11)	−0.113 (4)	0.7291 (14)	0.046 (6)*
C13	0.42833 (7)	−0.0078 (3)	0.59600 (12)	0.0357 (4)
H13	0.4529 (10)	−0.124 (3)	0.5793 (13)	0.038 (5)*
C14	0.40093 (8)	0.1454 (3)	0.53554 (10)	0.0350 (4)
H14	0.4049 (9)	0.147 (3)	0.4771 (12)	0.034 (5)*
C15	0.36560 (7)	0.3144 (2)	0.55973 (9)	0.0261 (3)
N1	0.33936 (6)	0.4614 (2)	0.49581 (7)	0.0321 (3)
C16	0.30656 (7)	0.6171 (3)	0.51960 (9)	0.0305 (3)
H16	0.2882 (11)	0.727 (4)	0.4726 (14)	0.046 (6)*
C17	0.29636 (7)	0.6412 (2)	0.60567 (9)	0.0240 (3)
H17	0.2724 (10)	0.761 (3)	0.6176 (12)	0.030 (5)*
C18	0.30834 (6)	0.5116 (2)	0.76227 (8)	0.0169 (2)
H18	0.3498 (8)	0.461 (3)	0.8088 (10)	0.014 (3)*
O18	0.29262 (5)	0.71674 (14)	0.78136 (6)	0.0218 (2)
HO18	0.3343 (11)	0.773 (3)	0.8182 (14)	0.042 (6)*
C19	0.24594 (6)	0.3711 (2)	0.75904 (7)	0.0157 (2)
H19	0.2561 (8)	0.240 (3)	0.7349 (11)	0.019 (4)*
C20	0.17458 (6)	0.4581 (2)	0.70350 (8)	0.0194 (2)
H20A	0.1621 (9)	0.396 (3)	0.6421 (12)	0.028 (4)*
H20B	0.1795 (10)	0.609 (3)	0.6954 (12)	0.032 (5)*
C21	0.11972 (6)	0.4111 (2)	0.75237 (8)	0.0200 (3)
H21	0.0733 (9)	0.452 (3)	0.7135 (10)	0.021 (4)*
C22	0.13710 (7)	0.5347 (3)	0.84042 (10)	0.0279 (3)
H22A	0.1034 (10)	0.495 (3)	0.8755 (12)	0.037 (5)*
H22B	0.1305 (11)	0.692 (4)	0.8235 (14)	0.049 (6)*
C23	0.21260 (7)	0.4864 (2)	0.89655 (8)	0.0215 (3)
H23A	0.2140 (10)	0.434 (3)	0.9576 (13)	0.036 (5)*
H23B	0.2430 (9)	0.597 (3)	0.8986 (12)	0.029 (4)*
N2	0.24091 (5)	0.3155 (2)	0.85177 (7)	0.0163 (2)
HN2	0.2898 (11)	0.277 (3)	0.8932 (13)	0.043 (5)*
C24	0.19405 (6)	0.1303 (2)	0.84168 (8)	0.0195 (2)
H24A	0.2189 (9)	0.024 (3)	0.8183 (11)	0.027 (4)*
H24B	0.1903 (9)	0.099 (3)	0.9014 (12)	0.031 (5)*
C25	0.12091 (6)	0.1809 (2)	0.77616 (8)	0.0195 (2)
H25	0.0852 (9)	0.164 (3)	0.8084 (11)	0.024 (4)*
C26	0.10192 (8)	0.0471 (2)	0.69356 (9)	0.0268 (3)
H26	0.1381 (9)	0.041 (3)	0.6593 (12)	0.031 (5)*
C27	0.04246 (10)	−0.0529 (3)	0.6656 (2)	0.0489 (5)
H27A	0.0075 (13)	−0.049 (4)	0.7001 (15)	0.055 (6)*
H27B	0.0312 (13)	−0.128 (4)	0.6114 (16)	0.059 (7)*
OW1	−0.08610 (6)	0.3448 (2)	−0.10042 (8)	0.0349 (3)
HW1A	−0.1005 (11)	0.444 (4)	−0.0757 (14)	0.043 (6)*
HW1B	−0.0884 (18)	0.245 (7)	−0.062 (2)	0.106 (12)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0137 (5)	0.0229 (6)	0.0147 (5)	0.0004 (5)	0.0058 (4)	0.0039 (4)
O1	0.0139 (4)	0.0213 (4)	0.0247 (4)	−0.0017 (3)	0.0000 (3)	0.0029 (4)
O2	0.0199 (4)	0.0259 (5)	0.0253 (4)	0.0053 (4)	0.0079 (3)	−0.0034 (4)
C2	0.0129 (5)	0.0192 (6)	0.0153 (5)	−0.0015 (4)	0.0031 (4)	0.0013 (4)
O3	0.0195 (4)	0.0309 (5)	0.0192 (4)	−0.0040 (4)	0.0053 (3)	−0.0077 (4)
C9	0.0141 (5)	0.0233 (6)	0.0159 (5)	−0.0067 (5)	0.0026 (4)	−0.0001 (5)
C10	0.0139 (5)	0.0285 (7)	0.0194 (5)	−0.0071 (5)	0.0045 (4)	−0.0041 (5)
C11	0.0158 (6)	0.0265 (7)	0.0283 (6)	−0.0038 (5)	0.0062 (5)	−0.0024 (5)
C12	0.0178 (6)	0.0291 (7)	0.0434 (8)	−0.0032 (6)	0.0081 (5)	−0.0080 (7)
C13	0.0221 (6)	0.0377 (9)	0.0491 (9)	−0.0073 (6)	0.0132 (6)	−0.0222 (8)
C14	0.0244 (7)	0.0533 (10)	0.0293 (7)	−0.0145 (7)	0.0109 (6)	−0.0213 (7)
C15	0.0184 (6)	0.0395 (8)	0.0207 (6)	−0.0123 (6)	0.0060 (5)	−0.0091 (6)
N1	0.0252 (6)	0.0531 (8)	0.0180 (5)	−0.0145 (6)	0.0062 (4)	−0.0032 (5)
C16	0.0250 (7)	0.0438 (9)	0.0201 (6)	−0.0106 (6)	0.0027 (5)	0.0063 (6)
C17	0.0203 (6)	0.0295 (7)	0.0203 (6)	−0.0051 (5)	0.0027 (5)	0.0043 (5)
C18	0.0156 (5)	0.0179 (6)	0.0162 (5)	−0.0004 (5)	0.0030 (4)	−0.0001 (4)
O18	0.0216 (4)	0.0170 (4)	0.0252 (5)	−0.0009 (3)	0.0040 (4)	−0.0022 (3)
C19	0.0148 (5)	0.0190 (6)	0.0127 (5)	0.0012 (4)	0.0029 (4)	0.0016 (4)
C20	0.0144 (5)	0.0235 (6)	0.0171 (5)	−0.0009 (5)	−0.0007 (4)	0.0033 (5)
C21	0.0133 (5)	0.0245 (7)	0.0200 (6)	0.0027 (4)	0.0015 (5)	−0.0022 (5)
C22	0.0203 (6)	0.0336 (8)	0.0264 (7)	0.0066 (6)	0.0015 (5)	−0.0103 (6)
C23	0.0183 (6)	0.0283 (7)	0.0173 (5)	0.0019 (5)	0.0042 (4)	−0.0058 (5)
N2	0.0137 (4)	0.0213 (5)	0.0138 (4)	−0.0002 (4)	0.0037 (4)	0.0005 (4)
C24	0.0147 (6)	0.0230 (6)	0.0202 (6)	−0.0027 (5)	0.0045 (4)	0.0033 (5)
C25	0.0133 (5)	0.0265 (7)	0.0189 (5)	−0.0025 (5)	0.0051 (4)	0.0007 (5)
C26	0.0272 (7)	0.0245 (7)	0.0250 (6)	−0.0030 (5)	0.0018 (5)	0.0000 (5)
C27	0.0346 (9)	0.0388 (9)	0.0615 (11)	−0.0073 (8)	−0.0048 (8)	−0.0168 (9)
OW1	0.0329 (5)	0.0208 (5)	0.0440 (6)	−0.0011 (5)	−0.0001 (5)	−0.0056 (5)

Geometric parameters (Å, º)

C1—O2	1.241 (2)	N1—C16	1.316 (2)
C1—O1	1.271 (2)	C16—C17	1.413 (2)
C1—C2	1.535 (2)	C18—O18	1.422 (2)
C2—O3	1.4156 (15)	C18—C19	1.535 (2)
C2—C2^i	1.542 (2)	C19—N2	1.5111 (14)
C9—C17	1.372 (2)	C19—C20	1.543 (2)
C9—C10	1.428 (2)	C20—C21	1.532 (2)
C9—C18	1.523 (2)	C21—C22	1.533 (2)
C10—C11	1.417 (2)	C21—C25	1.541 (2)
C10—C15	1.428 (2)	C22—C23	1.538 (2)
C11—C12	1.371 (2)	C23—N2	1.505 (2)
C12—C13	1.413 (2)	N2—C24	1.506 (2)
C13—C14	1.368 (3)	C24—C25	1.553 (2)
C14—C15	1.414 (2)	C25—C26	1.501 (2)
C15—N1	1.367 (2)	C26—C27	1.312 (2)
O2—C1—O1	125.55 (11)	C9—C17—C16	119.24 (14)
O2—C1—C2	117.42 (11)	O18—C18—C9	111.72 (10)
O1—C1—C2	117.00 (11)	O18—C18—C19	109.89 (10)
O3—C2—C1	110.74 (10)	C9—C18—C19	106.94 (9)
O3—C2—C2^i	110.83 (9)	N2—C19—C18	112.89 (9)
C1—C2—C2^i	107.93 (11)	N2—C19—C20	108.15 (9)
C17—C9—C10	118.52 (11)	C18—C19—C20	114.17 (10)
C17—C9—C18	120.21 (12)	C21—C20—C19	109.23 (10)
C10—C9—C18	121.20 (11)	C20—C21—C22	108.90 (11)
C11—C10—C15	118.59 (13)	C20—C21—C25	110.40 (10)
C11—C10—C9	124.00 (11)	C22—C21—C25	108.30 (11)
C15—C10—C9	117.40 (12)	C21—C22—C23	109.07 (10)
C12—C11—C10	121.00 (13)	N2—C23—C22	109.18 (10)
C11—C12—C13	120.25 (15)	C23—N2—C24	109.53 (10)
C14—C13—C12	120.10 (14)	C23—N2—C19	113.41 (10)
C13—C14—C15	121.14 (13)	C24—N2—C19	107.70 (9)
N1—C15—C14	117.98 (13)	N2—C24—C25	109.66 (10)
N1—C15—C10	123.11 (14)	C26—C25—C21	112.20 (10)
C14—C15—C10	118.91 (14)	C26—C25—C24	112.96 (11)
C16—N1—C15	117.03 (12)	C21—C25—C24	107.97 (10)
N1—C16—C17	124.68 (14)	C27—C26—C25	123.3 (2)
O2—C1—C2—O3	15.84 (14)	C10—C9—C18—C19	−79.00 (13)
O1—C1—C2—O3	−166.17 (10)	O18—C18—C19—N2	−77.73 (12)
O2—C1—C2—C2^i	−105.64 (10)	C9—C18—C19—N2	160.84 (10)
O1—C1—C2—C2^i	72.35 (10)	O18—C18—C19—C20	46.34 (13)
C17—C9—C10—C11	179.42 (11)	C9—C18—C19—C20	−75.09 (12)
C18—C9—C10—C11	−3.5 (2)	N2—C19—C20—C21	−13.27 (14)
C17—C9—C10—C15	−0.8 (2)	C18—C19—C20—C21	−139.85 (11)
C18—C9—C10—C15	176.23 (10)	C19—C20—C21—C22	67.40 (14)
C15—C10—C11—C12	−0.8 (2)	C19—C20—C21—C25	−51.38 (13)
C9—C10—C11—C12	178.93 (11)	C20—C21—C22—C23	−55.17 (15)
C10—C11—C12—C13	0.4 (2)	C25—C21—C22—C23	64.92 (14)
C11—C12—C13—C14	0.2 (2)	C21—C22—C23—N2	−6.9 (2)
C12—C13—C14—C15	−0.5 (2)	C22—C23—N2—C24	−57.15 (13)
C13—C14—C15—N1	−179.79 (13)	C22—C23—N2—C19	63.18 (13)
C13—C14—C15—C10	0.1 (2)	C18—C19—N2—C23	76.30 (12)
C11—C10—C15—N1	−179.59 (12)	C20—C19—N2—C23	−51.02 (13)
C9—C10—C15—N1	0.6 (2)	C18—C19—N2—C24	−162.34 (10)
C11—C10—C15—C14	0.6 (2)	C20—C19—N2—C24	70.35 (12)
C9—C10—C15—C14	−179.21 (11)	C23—N2—C24—C25	64.89 (12)
C14—C15—N1—C16	179.86 (12)	C19—N2—C24—C25	−58.88 (12)
C10—C15—N1—C16	0.0 (2)	C20—C21—C25—C26	−62.87 (13)
C15—N1—C16—C17	−0.5 (2)	C22—C21—C25—C26	177.99 (10)
C10—C9—C17—C16	0.4 (2)	C20—C21—C25—C24	62.25 (12)
C18—C9—C17—C16	−176.67 (11)	C22—C21—C25—C24	−56.89 (13)
N1—C16—C17—C9	0.3 (2)	N2—C24—C25—C26	118.74 (12)
C17—C9—C18—O18	−22.3 (2)	N2—C24—C25—C21	−5.92 (13)
C10—C9—C18—O18	160.73 (10)	C21—C25—C26—C27	−108.6 (2)
C17—C9—C18—C19	98.02 (13)	C24—C25—C26—C27	129.1 (2)

Symmetry code: (i) −x+1, y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—HO3···O2	0.80 (3)	2.14 (2)	2.638 (1)	120 (2)
O18—HO18···OW1^ii	0.94 (2)	1.78 (2)	2.709 (1)	171 (2)
N2—HN2···O1^iii	1.03 (2)	1.66 (2)	2.685 (1)	175 (2)
OW1—HW1A···O1^iv	0.84 (3)	1.87 (3)	2.692 (2)	166 (2)
OW1—HW1B···O2^v	0.89 (4)	2.06 (4)	2.931 (2)	167 (4)

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