Crystal structure of memantine–carb­oxy­borane

The crystal structure of a modified anti-Alzheimer's drug features O—H...O and N—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.062
• wR factor = 0.154
• Data-to-parameter ratio = 64.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT097_ALERT_2_B Large Reported Max.  (Positive) Residual Density       0.94 eA-3

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.94 Report
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00479 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N1       --H1A      .     Please Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         16 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT014_ALERT_1_G N.O.K.   _shelx_fab_checksum Found in CIF ......     Please Check
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.98 Why ?
PLAT606_ALERT_4_G VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          R Verify
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         30 Note
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law ( 1 0-2)         Est.d BASF       0.31 Check
PLAT931_ALERT_5_G CIFcalcFCF  Twin Law         [ 5 0 2] Est.d BASF       0.28 Check
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          7 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   3 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3,5-Dimethyladamantanylamine–boranecarboxylic acid

Crystal data

C13H24BNO2	F(000) = 1040
Mr = 237.14	Dx = 0.898 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 34.229 (4) Å	Cell parameters from 1799 reflections
b = 11.1051 (12) Å	θ = 2.9–25.6°
c = 9.2922 (10) Å	µ = 0.06 mm^−1
β = 96.526 (5)°	T = 100 K
V = 3509.3 (7) Å^3	Plate, colourless
Z = 8	0.32 × 0.30 × 0.10 mm

Data collection

Bruker APEXII Ultra diffractometer	10740 measured reflections
Radiation source: Micro Focus Rotating Anode, Bruker TXS	10740 independent reflections
Double Bounce Multilayer Mirrors monochromator	8531 reflections with I > 2σ(I)
Detector resolution: 8.258 pixels mm^-1	θmax = 25.7°, θmin = 1.2°
φ and ω scans	h = −41→41
Absorption correction: multi-scan (TWINABS; Bruker, 2012)	k = −13→13
Tmin = 0.300, Tmax = 0.333	l = −11→11

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 6.9836P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
10740 reflections	Δρmax = 0.94 e Å^−3
166 parameters	Δρmin = −0.24 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a two-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.54884 (6)	0.9933 (2)	1.1021 (3)	0.0296 (6)
H1	0.5259	1.0205	1.0994	0.044*
O2	0.52308 (7)	0.9168 (2)	0.8929 (2)	0.0373 (7)
N1	0.59334 (7)	0.8289 (2)	0.8033 (3)	0.0214 (6)
H1A	0.5763	0.7656	0.7974	0.026*
H1B	0.5825	0.8865	0.7416	0.026*
C9	0.61930 (9)	0.7507 (3)	0.5864 (3)	0.0203 (7)
H9A	0.5993	0.6859	0.5806	0.024*
H9B	0.6077	0.8209	0.5313	0.024*
C2	0.63037 (8)	0.7867 (3)	0.7461 (3)	0.0172 (7)
C10	0.64666 (9)	0.6768 (3)	0.8315 (4)	0.0224 (7)
H10A	0.6267	0.6120	0.8257	0.027*
H10B	0.6536	0.6983	0.9346	0.027*
C8	0.65553 (9)	0.7071 (3)	0.5192 (3)	0.0213 (7)
C11	0.68651 (9)	0.8083 (3)	0.5324 (4)	0.0241 (8)
H11A	0.7103	0.7806	0.4906	0.029*
H11B	0.6759	0.8793	0.4764	0.029*
C6	0.68384 (9)	0.6335 (3)	0.7642 (4)	0.0229 (8)
H6	0.6951	0.5618	0.8193	0.027*
C1	0.55232 (10)	0.9311 (3)	0.9806 (4)	0.0219 (8)
C4	0.69762 (9)	0.8445 (3)	0.6898 (4)	0.0243 (8)
C3	0.66090 (9)	0.8865 (3)	0.7553 (4)	0.0222 (7)
H3A	0.6681	0.9095	0.8578	0.027*
H3B	0.6498	0.9583	0.7023	0.027*
C7	0.67253 (9)	0.5977 (3)	0.6057 (4)	0.0225 (7)
H7A	0.6528	0.5323	0.6002	0.027*
H7B	0.6960	0.5676	0.5639	0.027*
C5	0.71424 (9)	0.7332 (3)	0.7751 (4)	0.0277 (8)
H5A	0.7383	0.7050	0.7354	0.033*
H5B	0.7214	0.7551	0.8780	0.033*
C13	0.64387 (10)	0.6749 (3)	0.3590 (4)	0.0298 (9)
H13A	0.6244	0.6099	0.3522	0.045*
H13B	0.6672	0.6484	0.3157	0.045*
H13C	0.6326	0.7458	0.3071	0.045*
C12	0.72819 (10)	0.9460 (3)	0.6973 (5)	0.0397 (10)
H12A	0.7515	0.9185	0.6543	0.060*
H12B	0.7358	0.9683	0.7988	0.060*
H12C	0.7169	1.0162	0.6438	0.060*
B1	0.59514 (12)	0.8823 (4)	0.9644 (4)	0.0295 (10)
H1C	0.6174 (10)	0.964 (3)	0.966 (4)	0.042 (10)*
H1D	0.6026 (11)	0.810 (3)	1.038 (4)	0.050 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0235 (12)	0.0335 (13)	0.0342 (14)	−0.0008 (11)	0.0140 (12)	−0.0136 (11)
O2	0.0334 (14)	0.0620 (17)	0.0167 (12)	0.0240 (13)	0.0038 (12)	−0.0048 (13)
N1	0.0202 (14)	0.0169 (13)	0.0280 (15)	0.0034 (11)	0.0062 (12)	0.0043 (12)
C9	0.0237 (18)	0.0150 (16)	0.0222 (17)	0.0018 (13)	0.0026 (15)	0.0029 (15)
C2	0.0149 (16)	0.0182 (16)	0.0190 (16)	0.0039 (13)	0.0043 (14)	−0.0018 (14)
C10	0.0236 (18)	0.0213 (17)	0.0230 (17)	0.0000 (14)	0.0062 (15)	0.0018 (15)
C8	0.0238 (18)	0.0177 (16)	0.0227 (18)	0.0022 (14)	0.0046 (15)	0.0007 (15)
C11	0.0225 (18)	0.0206 (17)	0.032 (2)	0.0023 (14)	0.0134 (16)	0.0027 (16)
C6	0.0221 (17)	0.0197 (16)	0.0268 (18)	0.0032 (14)	0.0027 (15)	0.0045 (15)
C1	0.030 (2)	0.0181 (17)	0.0183 (17)	0.0013 (14)	0.0046 (16)	0.0034 (15)
C4	0.0172 (17)	0.0215 (17)	0.035 (2)	−0.0027 (14)	0.0082 (16)	−0.0072 (16)
C3	0.0238 (18)	0.0193 (17)	0.0235 (17)	−0.0012 (14)	0.0024 (15)	−0.0002 (15)
C7	0.0214 (18)	0.0187 (16)	0.0287 (17)	0.0021 (14)	0.0079 (16)	−0.0043 (16)
C5	0.0170 (17)	0.037 (2)	0.0290 (19)	0.0053 (15)	0.0007 (16)	−0.0096 (18)
C13	0.033 (2)	0.033 (2)	0.023 (2)	0.0073 (17)	0.0038 (16)	0.0011 (17)
C12	0.027 (2)	0.036 (2)	0.058 (3)	−0.0085 (17)	0.012 (2)	−0.012 (2)
B1	0.025 (2)	0.037 (3)	0.028 (2)	0.0001 (19)	0.0062 (18)	−0.011 (2)

Geometric parameters (Å, º)

O1—H1	0.8400	C6—H6	1.0000
O1—C1	1.340 (4)	C6—C7	1.532 (5)
O2—C1	1.227 (4)	C6—C5	1.515 (4)
N1—H1A	0.9100	C1—B1	1.586 (5)
N1—H1B	0.9100	C4—C3	1.530 (4)
N1—C2	1.504 (4)	C4—C5	1.541 (4)
N1—B1	1.605 (5)	C4—C12	1.535 (4)
C9—H9A	0.9900	C3—H3A	0.9900
C9—H9B	0.9900	C3—H3B	0.9900
C9—C2	1.542 (4)	C7—H7A	0.9900
C9—C8	1.530 (4)	C7—H7B	0.9900
C2—C10	1.525 (4)	C5—H5A	0.9900
C2—C3	1.520 (4)	C5—H5B	0.9900
C10—H10A	0.9900	C13—H13A	0.9800
C10—H10B	0.9900	C13—H13B	0.9800
C10—C6	1.557 (4)	C13—H13C	0.9800
C8—C11	1.541 (4)	C12—H12A	0.9800
C8—C7	1.535 (4)	C12—H12B	0.9800
C8—C13	1.539 (5)	C12—H12C	0.9800
C11—H11A	0.9900	B1—H1C	1.19 (3)
C11—H11B	0.9900	B1—H1D	1.07 (4)
C11—C4	1.523 (5)
C1—O1—H1	109.5	O2—C1—O1	118.8 (3)
H1A—N1—H1B	106.9	O2—C1—B1	125.8 (3)
C2—N1—H1A	107.3	C11—C4—C3	109.6 (3)
C2—N1—H1B	107.3	C11—C4—C5	108.6 (3)
C2—N1—B1	120.0 (3)	C11—C4—C12	109.4 (3)
B1—N1—H1A	107.3	C3—C4—C5	108.2 (3)
B1—N1—H1B	107.3	C3—C4—C12	110.1 (3)
H9A—C9—H9B	108.1	C12—C4—C5	110.8 (3)
C2—C9—H9A	109.5	C2—C3—C4	110.2 (2)
C2—C9—H9B	109.5	C2—C3—H3A	109.6
C8—C9—H9A	109.5	C2—C3—H3B	109.6
C8—C9—H9B	109.5	C4—C3—H3A	109.6
C8—C9—C2	110.7 (2)	C4—C3—H3B	109.6
N1—C2—C9	107.2 (2)	H3A—C3—H3B	108.1
N1—C2—C10	109.8 (2)	C8—C7—H7A	109.7
N1—C2—C3	110.8 (2)	C8—C7—H7B	109.7
C10—C2—C9	109.2 (2)	C6—C7—C8	109.7 (3)
C3—C2—C9	109.6 (3)	C6—C7—H7A	109.7
C3—C2—C10	110.2 (2)	C6—C7—H7B	109.7
C2—C10—H10A	110.1	H7A—C7—H7B	108.2
C2—C10—H10B	110.1	C6—C5—C4	109.9 (3)
C2—C10—C6	107.8 (3)	C6—C5—H5A	109.7
H10A—C10—H10B	108.5	C6—C5—H5B	109.7
C6—C10—H10A	110.1	C4—C5—H5A	109.7
C6—C10—H10B	110.1	C4—C5—H5B	109.7
C9—C8—C11	108.6 (3)	H5A—C5—H5B	108.2
C9—C8—C7	108.3 (3)	C8—C13—H13A	109.5
C9—C8—C13	109.6 (3)	C8—C13—H13B	109.5
C7—C8—C11	108.6 (3)	C8—C13—H13C	109.5
C7—C8—C13	111.4 (3)	H13A—C13—H13B	109.5
C13—C8—C11	110.3 (3)	H13A—C13—H13C	109.5
C8—C11—H11A	109.4	H13B—C13—H13C	109.5
C8—C11—H11B	109.4	C4—C12—H12A	109.5
H11A—C11—H11B	108.0	C4—C12—H12B	109.5
C4—C11—C8	111.3 (3)	C4—C12—H12C	109.5
C4—C11—H11A	109.4	H12A—C12—H12B	109.5
C4—C11—H11B	109.4	H12A—C12—H12C	109.5
C10—C6—H6	109.0	H12B—C12—H12C	109.5
C7—C6—C10	109.7 (3)	N1—B1—H1C	104.6 (18)
C7—C6—H6	109.0	N1—B1—H1D	107 (2)
C5—C6—C10	109.5 (3)	C1—B1—N1	106.1 (3)
C5—C6—H6	109.0	C1—B1—H1C	109.7 (16)
C5—C6—C7	110.5 (3)	C1—B1—H1D	111 (2)
O1—C1—B1	115.4 (3)	H1C—B1—H1D	118 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.84	1.82	2.662 (3)	176
N1—H1B···O1^ii	0.91	2.11	3.011 (3)	171

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