organic compounds
`
`Acta Crystallographica Section C
`Crystal Structure
`Communications
`
`ISSN 0108-2701
`
`N-(2-Hydroxyethyl)ethylene-
`diammonium hydrogenphosphate
`monohydrate
`
`Selcuk Demir,a Veysel T. Yilmaz,a* Omer Andaca and
`William T. A. Harrisonb
`
`aDepartment of Chemistry, Faculty of Arts and Science, Ondokuz Mayis University,
`55139 Kurupelit Samsun, Turkey, and bDepartment of Chemistry, University of
`Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
`Correspondence e-mail: vtyilmaz@omu.edu.tr
`
`Figure 1
`A view of the molecule of (I) with 50% probability displacement
`ellipsoids. H atoms are drawn as small spheres of arbitrary radii and
`hydrogen bonds are indicated by dashed lines.
`
`Received 7 May 2002
`Accepted 28 May 2002
`Online 20 June 2002
`
`2(cid:255)(cid:1)H2O, contains
`The title compound, C4H14N2O2+(cid:1)HPO4
`alternating interleaved layers of hydrogenphosphate and N-
`(2-hydroxyethyl)ethylenediammonium moieties. The water
`molecules are associated with channel-like voids in the
`structure and a network of hydrogen bonds stabilizes the
`crystal packing.
`
`Comment
`
`During the synthesis of metal phosphates templated by
`organic amines (Cheetham et al., 1999), amine phosphates may
`occur as unexpected side products and may also act as inter-
`mediates in the formation of open-framework structures
`(Oliver et al., 1998; Neeraj et al., 1999). We describe here the
`structure of one such amine phosphate, namely the title
`compound, (I).
`
`The structure of (I) (Fig. 1) consists of a molecular network.
`Both amino groups of
`the N-(2-hydroxyethyl)ethylenedi-
`ammonium moiety are protonated, resulting in a divalent
`species. The N-(2-hydroxyethyl)ethylenediammonium cation
`exhibits a gauche conformation and bond distances within the
`cation are comparable with those in the neutral molecule
`coordinated to CuII and CdII ions (Yilmaz et al., 2002). One of
`the phosphate P—O vertices is protonated and shows the
`expected lengthening relative to the other P—O bonds (Oliver
`et al., 1998).
`The crystal packing in (I) is shown in Fig. 2. The structure
`contains alternating interleaved layers of anions and cations,
`
`Figure 2
`A projection of the structure of (I) along [001].
`
`with the layers propagating in the (101) plane. The water
`molecules occupy channel-like voids propagating along [001].
`All the H atoms of the ammonium groups form N—H(cid:1)(cid:1)(cid:1)O
`hydrogen bonds to neighbouring phosphate O atoms, while
`the hydroxyl group of the organic species forms hydrogen
`bonds to the O atoms of both the phosphate ions and water
`molecules. Adjacent phosphate anions are also linked by P—
`OH(cid:1)(cid:1)(cid:1)O hydrogen bonds in the [001] direction.
`
`Experimental
`
`H3PO4 (0.814 ml, 12 mmol) (aqueous, 85% w/w) was added dropwise
`to an aqueous solution of ethylene glycol (20%, 20 ml) with N-(2-
`hydroxyethyl)ethylenediamine (1.012 ml, 10 mmol) and the resulting
`solution was stirred for 2 h at 323 K. The mixture was then left to
`crystallize at room temperature. Colourless chunk-type crystals of (I)
`were formed, and these were washed with a small amount of water
`and acetone, and dried in air.
`
`Acta Cryst. (2002). C58, o407–o408
`
`DOI: 10.1107/S0108270102009629
`
`# 2002 International Union of Crystallography o407
`
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`organic compounds
`
`Table 1
`Selected geometric parameters (A˚ , (cid:14)).
`
`1.5144 (8)
`1.5402 (7)
`1.5247 (8)
`1.5862 (8)
`1.4179 (16)
`
`(cid:255)179.52 (10)
`(cid:255)71.91 (14)
`
`N1—C2
`N1—C3
`N2—C4
`C1—C2
`C3—C4
`
`1.4875 (15)
`1.4933 (13)
`1.4857 (13)
`1.5178 (17)
`1.5162 (16)
`
`C2—N1—C3—C4
`N1—C3—C4—N2
`
`174.46 (9)
`82.13 (11)
`
`P1—O1
`P1—O2
`P1—O3
`P1—O4
`O5—C1
`
`C3—N1—C2—C1
`O5—C1—C2—N1
`
`Crystal data
`C4H14N2O2+(cid:1)HPO4
`Mr = 220.17
`Monoclinic, P21=c
`a = 7.0863 (3) A˚
`b = 28.4885 (11) A˚
`c = 4.8336 (2) A˚
`(cid:12) = 94.874 (1)(cid:14)
`V = 972.27 (7) A˚ 3
`Z = 4
`
`Data collection
`
`2(cid:255)(cid:1)H2O
`
`Bruker SMART 1000 CCD area-
`detector diffractometer
`! scans
`Absorption correction: multi-scan
`(SADABS; Bruker, 1999)
`Tmin = 0.902, Tmax = 0.947
`9939 measured reflections
`
`Refinement
`
`Refinement on F 2
`R[F 2 > 2(cid:27)(F 2)] = 0.032
`wR(F 2) = 0.091
`S = 1.10
`3520 reflections
`162 parameters
`H atoms treated by a mixture of
`independent and constrained
`refinement
`
`Dx = 1.504 Mg m(cid:255)3
`Mo K(cid:11) radiation
`Cell parameters from 5486
`reflections
`(cid:18) = 2.9–32.5(cid:14)
`(cid:22) = 0.29 mm(cid:255)1
`T = 293 (2) K
`Chunk, colourless
`0.46 (cid:2) 0.30 (cid:2) 0.19 mm
`
`3520 independent reflections
`3051 reflections with I > 2(cid:27)(I)
`Rint = 0.016
`(cid:18)max = 32.5(cid:14)
`h = (cid:255)10 ! 10
`k = (cid:255)43 ! 34
`l = (cid:255)6 ! 7
`
`2) + (0.0512P)2
`w = 1/[(cid:27)2(Fo
`+ 0.0694P]
`
`2 + 2Fc2)/3
`where P = (Fo
`((cid:1)/(cid:27))max < 0.001
`(cid:1)(cid:26)max = 0.34 e A˚ (cid:255)3
`(cid:1)(cid:26)min = (cid:255)0.25 e A˚ (cid:255)3
`
`Water, hydroxyl and amine H atoms were found in difference maps
`and refined freely. H atoms bonded to C atoms were placed in
`calculated positions (C—H = 0.97 A˚ ) and treated as riding.
`
`D—H
`
`D(cid:1)(cid:1)(cid:1)A
`
`D—H(cid:1)(cid:1)(cid:1)A
`
`Table 2
`Hydrogen-bonding geometry (A˚ , (cid:14)).
`D—H(cid:1)(cid:1)(cid:1)A
`H(cid:1)(cid:1)(cid:1)A
`O4—H4(cid:1)(cid:1)(cid:1)O1i
`0.80 (3)
`1.82 (3)
`2.5947 (11)
`163 (3)
`O5—H5(cid:1)(cid:1)(cid:1)O3
`0.77 (2)
`1.86 (2)
`2.6228 (13)
`174 (2)
`O1W—H1A(cid:1)(cid:1)(cid:1)O5
`0.83 (3)
`1.95 (3)
`2.7731 (15)
`172 (2)
`O1W—H1B(cid:1)(cid:1)(cid:1)O1Wii
`0.83 (2)
`2.00 (2)
`2.8227 (14)
`170 (2)
`N1—H111(cid:1)(cid:1)(cid:1)O2
`0.881 (16)
`1.898 (17)
`2.7674 (12)
`169 (2)
`N1—H112(cid:1)(cid:1)(cid:1)O2i
`0.832 (18)
`1.905 (18)
`2.7046 (12)
`161 (2)
`N2—H211(cid:1)(cid:1)(cid:1)O1iii
`0.920 (18)
`1.846 (18)
`2.7643 (13)
`175 (2)
`N2—H212(cid:1)(cid:1)(cid:1)O3iv
`0.876 (18)
`1.875 (18)
`2.7412 (12)
`169 (2)
`N2—H213(cid:1)(cid:1)(cid:1)O2
`0.897 (16)
`1.994 (17)
`2.8584 (12)
`162 (2)
`
`
`Symmetry codes: (i) x; y; z (cid:255) 1; (ii) x; 12 (cid:255) y; 12 (cid:135) z; (iii) (cid:255)x;(cid:255)y; 1 (cid:255) z; (iv) x (cid:255) 1; y; z.
`
`Data collection: SMART (Bruker, 1999); cell refinement: SAINT
`(Bruker, 1999); data reduction: SAINT; program(s) used to solve
`structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine
`structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
`ORTEP-3 for Windows (Farrugia, 1997); software used to prepare
`material for publication: SHELXL97.
`
`The authors thank Ondokuz Mayis University for the
`financial support given to the project.
`
`Supplementary data for this paper are available from the IUCr electronic
`archives (Reference: AV1110). Services for accessing these data are
`described at the back of the journal.
`
`References
`
`Bruker (1999). SADABS, SMART (Version 5.624) and SAINT (Version
`6.02A). Bruker AXS Inc., Madison, Wisconsin, USA.
`Cheetham, A. K., Ferey, G. & Loiseau, T. (1999). Angew. Chem. Int. Ed. 38,
`3268–3292.
`Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
`Neeraj, S., Natarajan, S. & Rao, C. N. R. (1999). Angew. Chem. Int. Ed. 38,
`3480–3483.
`Oliver, S., Lough, A. J. & Ozin, G. A. (1998). Inorg. Chem. 37, 5021–
`5028.
`Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473.
`Sheldrick, G. M. (1997). SHELXL97. University of Go¨ ttingen, Germany.
`Yilmaz, V. T., Karadag, A. & Thoene, C. (2002). J. Coord. Chem. 55, 609–
`618.
`
`o408 Selcuk Demir et al.
`
`
`
`(cid:15) C4H14N2O2+(cid:1)HPO42(cid:255)(cid:1)H2O
`
`Acta Cryst. (2002). C58, o407–o408
`
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`supporting information
`
`supporting information
`
`Acta Cryst. (2002). C58, o407–o408 [doi:10.1107/S0108270102009629]
`
`N-(2-Hydroxyethyl)ethylenediammonium hydrogenphosphate monohydrate
`
`Selcuk Demir, Veysel T. Yilmaz, Omer Andac and William T. A. Harrison
`
`Computing details
`
`Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used
`to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997);
`molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication:
`SHELXL97.
`
`N-(2-hydroxyethyl)ethylenediammonium hydrogenphosphate monohydrate
`
`Crystal data
`C4H14N2O2+·HO4P2−·H2O
`Mr = 220.17
`Monoclinic, P21/c
`a = 7.0863 (3) Å
`b = 28.4885 (11) Å
`c = 4.8336 (2) Å
`β = 94.874 (1)°
`V = 972.27 (7) Å3
`Z = 4
`F(000) = 472
`
`Data collection
`Bruker SMART 1000 CCD area-detector
`diffractometer
`Radiation source: fine-focus sealed tube
`Graphite monochromator
`ω scans
`Absorption correction: multi-scan
`(SADABS; Bruker, 1999)
`Tmin = 0.902, Tmax = 0.947
`
`Refinement
`Refinement on F2
`Least-squares matrix: full
`R[F2 > 2σ(F2)] = 0.032
`wR(F2) = 0.091
`S = 1.10
`3520 reflections
`162 parameters
`0 restraints
`Primary atom site location: structure-invariant
`direct methods
`
`Dx = 1.504 Mg m−3
`Melting point: not measured K
`Mo Kα radiation, λ = 0.71073 Å
`Cell parameters from 5486 reflections
`θ = 2.9–32.5°
`µ = 0.29 mm−1
`T = 293 K
`Chunk, colourless
`0.46 × 0.30 × 0.19 mm
`
`9939 measured reflections
`3520 independent reflections
`3051 reflections with I > 2σ(I)
`Rint = 0.016
`θmax = 32.5°, θmin = 2.9°
`h = −10→10
`k = −43→34
`l = −6→7
`
`Secondary atom site location: none
`Hydrogen site location: mixed
`H atoms treated by a mixture of independent
`and constrained refinement
`w = 1/[σ2(Fo2) + (0.0512P)2 + 0.0694P]
`
`
`where P = (Fo2 + 2Fc
`2)/3
`(Δ/σ)max < 0.001
`Δρmax = 0.34 e Å−3
`Δρmin = −0.25 e Å−3
`
`Acta Cryst. (2002). C58, o407–o408
`
`sup-1
`
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`
`Special details
`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)
`
`P1
`O1
`O2
`O3
`O4
`H4
`O5
`H5
`O1W
`H1A
`H1B
`N1
`H111
`H112
`N2
`H211
`H212
`H213
`C1
`H11
`H12
`C2
`H21
`H22
`C3
`H31
`H32
`C4
`H4A
`H4B
`
`x
`
`0.24386 (3)
`0.29299 (11)
`0.06383 (10)
`0.40488 (10)
`0.19514 (14)
`0.227 (4)
`0.32252 (15)
`0.346 (3)
`0.67791 (16)
`0.572 (4)
`0.667 (3)
`−0.01794 (12)
`0.022 (2)
`0.027 (2)
`−0.27371 (12)
`−0.278 (2)
`−0.371 (2)
`−0.167 (2)
`0.25351 (17)
`0.3124
`0.2891
`0.03989 (17)
`−0.0190
`−0.0038
`−0.22630 (14)
`−0.2751
`−0.2887
`−0.27073 (14)
`−0.3932
`−0.1766
`
`y
`
`0.066713 (9)
`0.03924 (3)
`0.09652 (3)
`0.09761 (3)
`0.02854 (3)
`0.0375 (10)
`0.18549 (3)
`0.1595 (7)
`0.22440 (5)
`0.2120 (9)
`0.2415 (8)
`0.13671 (3)
`0.1264 (6)
`0.1211 (6)
`0.05690 (4)
`0.0247 (6)
`0.0689 (6)
`0.0633 (6)
`0.19171 (5)
`0.1687
`0.2227
`0.18656 (4)
`0.2055
`0.1979
`0.12816 (4)
`0.1413
`0.1438
`0.07612 (4)
`0.0708
`0.0593
`
`z
`
`0.53198 (5)
`0.79651 (15)
`0.54860 (15)
`0.44708 (16)
`0.29789 (17)
`0.152 (5)
`0.3287 (2)
`0.351 (4)
`0.4570 (2)
`0.435 (5)
`0.595 (5)
`0.03106 (18)
`0.198 (3)
`−0.094 (4)
`0.27835 (19)
`0.264 (3)
`0.354 (4)
`0.385 (3)
`0.0471 (3)
`−0.0661
`−0.0138
`0.0031 (3)
`0.1386
`−0.1804
`−0.0113 (2)
`−0.1882
`0.1339
`−0.0070 (2)
`−0.1076
`−0.1026
`
`Uiso*/Ueq
`0.01795 (7)
`0.02687 (16)
`0.02467 (15)
`0.02603 (16)
`0.0344 (2)
`0.090 (8)*
`0.0384 (2)
`0.050 (5)*
`0.0462 (3)
`0.074 (7)*
`0.069 (7)*
`0.02173 (16)
`0.036 (4)*
`0.038 (4)*
`0.02369 (17)
`0.038 (4)*
`0.040 (4)*
`0.035 (4)*
`0.0361 (3)
`0.053 (5)*
`0.045 (5)*
`0.0328 (2)
`0.049 (5)*
`0.050 (5)*
`0.0261 (2)
`0.040 (4)*
`0.052 (5)*
`0.0252 (2)
`0.040 (4)*
`0.038 (4)*
`
`Atomic displacement parameters (Å2)
`
`U11
`
`U22
`
`U33
`
`U12
`
`U13
`
`U23
`
`P1
`O1
`
`0.01798 (11)
`0.0317 (4)
`
`0.02074 (13)
`0.0298 (4)
`
`0.01533 (11)
`0.0188 (3)
`
`−0.00010 (8)
`0.0015 (3)
`
`0.00256 (7)
`0.0009 (3)
`
`−0.00059 (8)
`0.0046 (3)
`
`Acta Cryst. (2002). C58, o407–o408
`
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`
`0.0249 (3)
`0.0324 (4)
`0.0213 (4)
`0.0400 (5)
`0.0438 (6)
`0.0215 (4)
`0.0238 (4)
`0.0368 (6)
`0.0397 (6)
`0.0279 (5)
`0.0202 (4)
`
`0.0035 (3)
`−0.0010 (3)
`−0.0118 (4)
`−0.0064 (4)
`−0.0040 (5)
`0.0001 (3)
`−0.0008 (3)
`−0.0120 (5)
`−0.0021 (4)
`0.0027 (4)
`−0.0049 (4)
`
`0.0023 (2)
`0.0074 (3)
`0.0108 (3)
`−0.0119 (4)
`0.0006 (4)
`0.0009 (3)
`0.0027 (3)
`−0.0026 (5)
`−0.0048 (5)
`−0.0001 (3)
`−0.0003 (3)
`
`−0.0001 (3)
`0.0029 (3)
`−0.0072 (3)
`0.0015 (3)
`−0.0047 (5)
`−0.0001 (3)
`0.0011 (3)
`0.0073 (5)
`0.0045 (4)
`0.0035 (4)
`−0.0009 (3)
`
`O2
`O3
`O4
`O5
`O1W
`N1
`N2
`C1
`C2
`C3
`C4
`
`0.0181 (3)
`0.0202 (3)
`0.0533 (5)
`0.0470 (5)
`0.0382 (5)
`0.0220 (4)
`0.0200 (4)
`0.0363 (6)
`0.0357 (6)
`0.0212 (4)
`0.0247 (4)
`
`0.0311 (4)
`0.0264 (4)
`0.0300 (4)
`0.0253 (4)
`0.0562 (7)
`0.0214 (4)
`0.0274 (5)
`0.0342 (6)
`0.0215 (5)
`0.0288 (5)
`0.0302 (5)
`
`Geometric parameters (Å, º)
`
`P1—O1
`P1—O2
`P1—O3
`P1—O4
`O4—H4
`O5—C1
`O5—H5
`O1W—H1A
`O1W—H1B
`N1—C2
`N1—C3
`N1—H111
`N1—H112
`N2—C4
`
`O1—P1—O3
`O1—P1—O2
`O3—P1—O2
`O1—P1—O4
`O3—P1—O4
`O2—P1—O4
`P1—O4—H4
`C1—O5—H5
`H1A—O1W—H1B
`C2—N1—C3
`C2—N1—H111
`C3—N1—H111
`C2—N1—H112
`C3—N1—H112
`H111—N1—H112
`C4—N2—H211
`C4—N2—H212
`H211—N2—H212
`C4—N2—H213
`
`1.5144 (8)
`1.5402 (7)
`1.5247 (8)
`1.5862 (8)
`0.80 (3)
`1.4179 (16)
`0.77 (2)
`0.83 (3)
`0.83 (2)
`1.4875 (15)
`1.4933 (13)
`0.881 (16)
`0.832 (18)
`1.4857 (13)
`
`113.71 (4)
`111.90 (4)
`109.75 (5)
`105.57 (5)
`109.05 (5)
`106.51 (5)
`110 (2)
`108.1 (15)
`102 (2)
`114.85 (9)
`109.4 (10)
`107.9 (10)
`108.6 (12)
`104.2 (11)
`111.7 (15)
`107.4 (10)
`108.4 (11)
`113.6 (14)
`112.2 (10)
`
`N2—H211
`N2—H212
`N2—H213
`C1—C2
`C1—H11
`C1—H12
`C2—H21
`C2—H22
`C3—C4
`C3—H31
`C3—H32
`C4—H4A
`C4—H4B
`
`C2—C1—H11
`O5—C1—H12
`C2—C1—H12
`H11—C1—H12
`N1—C2—C1
`N1—C2—H21
`C1—C2—H21
`N1—C2—H22
`C1—C2—H22
`H21—C2—H22
`N1—C3—C4
`N1—C3—H31
`C4—C3—H31
`N1—C3—H32
`C4—C3—H32
`H31—C3—H32
`N2—C4—C3
`N2—C4—H4A
`C3—C4—H4A
`
`0.920 (18)
`0.876 (18)
`0.897 (16)
`1.5178 (17)
`0.9700
`0.9700
`0.9700
`0.9700
`1.5162 (16)
`0.9700
`0.9700
`0.9700
`0.9700
`
`109.1
`109.1
`109.1
`107.9
`111.03 (10)
`109.4
`109.4
`109.4
`109.4
`108.0
`111.21 (9)
`109.4
`109.4
`109.4
`109.4
`108.0
`113.12 (9)
`109.0
`109.0
`
`Acta Cryst. (2002). C58, o407–o408
`
`sup-3
`
`Merck Exhibit 2213, Page 5
`Mylan Pharmaceuticals Inc. v. Merck Sharp & Dohme Corp.
`IPR2020-00040
`
`

`

`supporting information
`
`H211—N2—H213
`H212—N2—H213
`O5—C1—C2
`O5—C1—H11
`
`C3—N1—C2—C1
`O5—C1—C2—N1
`
`105.6 (14)
`109.7 (16)
`112.40 (11)
`109.1
`
`N2—C4—H4B
`C3—C4—H4B
`H4A—C4—H4B
`
`109.0
`109.0
`107.8
`
`−179.52 (10)
`−71.91 (14)
`
`C2—N1—C3—C4
`N1—C3—C4—N2
`
`174.46 (9)
`82.13 (11)
`
`Hydrogen-bond geometry (Å, º)
`
`D—H···A
`
`O4—H4···O1i
`O5—H5···O3
`O1W—H1A···O5
`O1W—H1B···O1Wii
`N1—H111···O2
`N1—H112···O2i
`N2—H211···O1iii
`N2—H212···O3iv
`N2—H213···O2
`
`D—H
`
`0.80 (3)
`0.77 (2)
`0.83 (3)
`0.83 (2)
`0.881 (16)
`0.832 (18)
`0.920 (18)
`0.876 (18)
`0.897 (16)
`
`H···A
`
`1.82 (3)
`1.86 (2)
`1.95 (3)
`2.00 (2)
`1.898 (17)
`1.905 (18)
`1.846 (18)
`1.875 (18)
`1.994 (17)
`
`D···A
`
`2.5947 (11)
`2.6228 (13)
`2.7731 (15)
`2.8227 (14)
`2.7674 (12)
`2.7046 (12)
`2.7643 (13)
`2.7412 (12)
`2.8584 (12)
`
`D—H···A
`
`163 (3)
`174 (2)
`172 (2)
`170 (2)
`169 (2)
`161 (2)
`175 (2)
`169 (2)
`162 (2)
`
`Symmetry codes: (i) x, y, z−1; (ii) x, −y+1/2, z+1/2; (iii) −x, −y, −z+1; (iv) x−1, y, z.
`
`Acta Cryst. (2002). C58, o407–o408
`
`sup-4
`
`Merck Exhibit 2213, Page 6
`Mylan Pharmaceuticals Inc. v. Merck Sharp & Dohme Corp.
`IPR2020-00040
`
`