Crystal structure of dimethyl N,N′-[(ethyne-1,2-di­yl)bis­(1,4-phenyl­enecarbon­yl)]bis­(L-alaninate)

The title compound shows a mol­ecular framework with the di­phenyl­ethyne unit slightly deviating from planarity and the L-alanine moieties adopting a distorted helical conformation. The crystal structure features a two-dimensional network supported by N—H...O and C—H...O hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.055
• wR factor = 0.125
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Non-Solv.  Resd 1  H   Uiso(max)/Uiso(min) Range        4.1 Ratio
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00571 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         85 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C9       - C12      .       1.43 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C13      - C14      .       1.43 Ang.
PLAT791_ALERT_4_G Model has Chirality at C2          (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C22         (Chiral SPGR)          S Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         15 Note

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

   1 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
   5 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

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Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

N,N'-[(Ethyne-1,2-diyl)bis(1,4-phenylenecarbonyl)]bis(L-alaninate)

Crystal data

C24H24N2O6	F(000) = 460
Mr = 436.45	Dx = 1.310 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 4.9409 (4) Å	Cell parameters from 2881 reflections
b = 39.015 (3) Å	θ = 3.6–26.5°
c = 5.8447 (4) Å	µ = 0.10 mm^−1
β = 100.905 (3)°	T = 153 K
V = 1106.34 (14) Å^3	Irregular, colourless
Z = 2	0.25 × 0.18 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer	3859 reflections with I > 2σ(I)
Radiation source: sealed x-ray tube	Rint = 0.034
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −4→6
Tmin = 0.977, Tmax = 0.988	k = −52→49
10506 measured reflections	l = −7→7
5192 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.055	w = 1/[σ^2(Fo^2) + (0.0519P)^2 + 0.3338P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.125	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.16 e Å^−3
5192 reflections	Δρmin = −0.23 e Å^−3
302 parameters	Absolute structure: Refined as an inversion twin
3 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 2-component inversion twin.

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

	x	y	z	Uiso*/Ueq
O1	−0.3228 (6)	0.27103 (7)	1.3737 (5)	0.0359 (7)
O2	−0.1565 (8)	0.36026 (8)	1.6451 (5)	0.0492 (9)
O3	0.0032 (6)	0.34262 (6)	1.3334 (5)	0.0351 (7)
O4	0.6614 (6)	0.01503 (7)	0.0365 (6)	0.0438 (8)
O5	0.5951 (6)	−0.06167 (7)	−0.1874 (5)	0.0332 (6)
O6	0.4374 (6)	−0.05575 (7)	0.1439 (5)	0.0372 (7)
N1	0.1280 (7)	0.27972 (8)	1.5074 (6)	0.0262 (7)
H1	0.301 (4)	0.2773 (9)	1.489 (6)	0.016 (9)*
N2	0.2024 (7)	0.00595 (8)	−0.0317 (6)	0.0275 (7)
H2	0.039 (5)	0.0127 (12)	−0.002 (8)	0.044 (13)*
C1	0.3251 (9)	0.31396 (11)	1.8526 (7)	0.0395 (10)
H1A	0.3866	0.2931	1.9401	0.059*
H1B	0.2791	0.3314	1.9594	0.059*
H1C	0.4728	0.3225	1.7771	0.059*
C2	0.0727 (8)	0.30608 (9)	1.6691 (7)	0.0279 (8)
H2A	−0.0708	0.2968	1.7520	0.034*
C3	−0.0422 (8)	0.33900 (9)	1.5482 (7)	0.0283 (8)
C4	−0.1041 (10)	0.37401 (11)	1.2158 (7)	0.0420 (11)
H4A	−0.2869	0.3789	1.2501	0.063*
H4B	−0.1182	0.3713	1.0473	0.063*
H4C	0.0206	0.3931	1.2708	0.063*
C5	−0.0835 (8)	0.26402 (9)	1.3680 (7)	0.0251 (8)
C6	−0.0077 (8)	0.23641 (9)	1.2131 (7)	0.0272 (9)
C7	0.2173 (9)	0.21521 (9)	1.2828 (7)	0.0299 (9)
H7	0.3311	0.2183	1.4316	0.036*
C8	0.2781 (8)	0.18931 (10)	1.1366 (7)	0.0312 (9)
H8	0.4310	0.1746	1.1878	0.037*
C9	0.1184 (8)	0.18472 (9)	0.9175 (7)	0.0293 (8)
C10	−0.1098 (9)	0.20622 (10)	0.8463 (8)	0.0356 (10)
H10	−0.2211	0.2035	0.6960	0.043*
C11	−0.1735 (9)	0.23150 (10)	0.9951 (7)	0.0320 (9)
H11	−0.3313	0.2455	0.9477	0.038*
C12	0.1832 (9)	0.15849 (9)	0.7647 (7)	0.0309 (9)
C13	0.2348 (9)	0.13652 (10)	0.6362 (7)	0.0327 (9)
C14	0.2895 (9)	0.10953 (10)	0.4845 (7)	0.0308 (9)
C15	0.5208 (9)	0.08859 (11)	0.5503 (8)	0.0402 (11)
H15	0.6465	0.0928	0.6918	0.048*
C16	0.5651 (9)	0.06161 (11)	0.4073 (8)	0.0414 (11)
H16	0.7246	0.0477	0.4506	0.050*
C17	0.3828 (8)	0.05450 (9)	0.2040 (7)	0.0275 (8)
C18	0.1575 (9)	0.07580 (10)	0.1360 (8)	0.0353 (10)
H18	0.0335	0.0716	−0.0065	0.042*
C19	0.1123 (9)	0.10325 (10)	0.2755 (8)	0.0366 (10)
H19	−0.0417	0.1179	0.2269	0.044*
C20	0.4274 (8)	0.02379 (9)	0.0616 (7)	0.0287 (9)
C21	0.2291 (10)	−0.01405 (12)	−0.4265 (7)	0.0432 (11)
H21A	0.0730	0.0008	−0.4902	0.065*
H21B	0.2231	−0.0348	−0.5222	0.065*
H21C	0.4019	−0.0018	−0.4272	0.065*
C22	0.2127 (8)	−0.02395 (9)	−0.1792 (6)	0.0266 (8)
H22	0.0349	−0.0365	−0.1866	0.032*
C23	0.4398 (8)	−0.04847 (9)	−0.0795 (6)	0.0260 (8)
C24	0.6460 (10)	−0.07959 (11)	0.2541 (7)	0.0441 (11)
H24A	0.6093	−0.1023	0.1831	0.066*
H24B	0.6422	−0.0810	0.4209	0.066*
H24C	0.8278	−0.0716	0.2330	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0247 (15)	0.0326 (15)	0.0523 (18)	0.0022 (12)	0.0120 (13)	−0.0084 (13)
O2	0.077 (2)	0.0366 (17)	0.0371 (17)	0.0282 (16)	0.0196 (17)	0.0017 (13)
O3	0.0475 (18)	0.0253 (14)	0.0347 (16)	0.0060 (13)	0.0135 (13)	0.0029 (12)
O4	0.0220 (16)	0.0335 (16)	0.080 (2)	−0.0023 (12)	0.0185 (15)	−0.0213 (15)
O5	0.0339 (16)	0.0292 (14)	0.0390 (15)	0.0031 (12)	0.0135 (12)	−0.0066 (12)
O6	0.0442 (18)	0.0350 (16)	0.0353 (16)	0.0093 (13)	0.0149 (13)	0.0002 (12)
N1	0.0209 (17)	0.0217 (16)	0.0377 (18)	0.0026 (13)	0.0095 (14)	−0.0032 (13)
N2	0.0225 (17)	0.0262 (16)	0.0347 (18)	0.0016 (14)	0.0077 (14)	−0.0056 (14)
C1	0.035 (2)	0.042 (2)	0.039 (2)	0.011 (2)	−0.0006 (19)	−0.0103 (19)
C2	0.030 (2)	0.0208 (17)	0.036 (2)	0.0049 (16)	0.0149 (17)	−0.0025 (16)
C3	0.031 (2)	0.0214 (18)	0.033 (2)	0.0027 (16)	0.0076 (17)	−0.0020 (16)
C4	0.063 (3)	0.027 (2)	0.035 (2)	0.008 (2)	0.008 (2)	0.0057 (18)
C5	0.025 (2)	0.0184 (16)	0.033 (2)	−0.0008 (15)	0.0086 (16)	−0.0001 (15)
C6	0.030 (2)	0.0154 (17)	0.037 (2)	0.0006 (15)	0.0098 (18)	0.0013 (15)
C7	0.032 (2)	0.0203 (19)	0.036 (2)	0.0031 (16)	0.0037 (17)	−0.0041 (16)
C8	0.034 (2)	0.0200 (18)	0.039 (2)	0.0081 (17)	0.0074 (17)	−0.0035 (17)
C9	0.038 (2)	0.0143 (17)	0.037 (2)	0.0024 (16)	0.0117 (17)	0.0010 (15)
C10	0.038 (2)	0.030 (2)	0.037 (2)	0.0063 (18)	0.0044 (18)	−0.0042 (17)
C11	0.030 (2)	0.028 (2)	0.037 (2)	0.0093 (18)	0.0031 (18)	−0.0013 (17)
C12	0.039 (2)	0.0193 (18)	0.034 (2)	0.0031 (16)	0.0066 (17)	−0.0016 (16)
C13	0.037 (2)	0.0241 (19)	0.039 (2)	0.0021 (18)	0.0112 (18)	−0.0001 (18)
C14	0.036 (2)	0.0209 (18)	0.037 (2)	−0.0002 (16)	0.0104 (18)	−0.0053 (16)
C15	0.039 (3)	0.032 (2)	0.046 (3)	0.0033 (19)	−0.003 (2)	−0.0124 (19)
C16	0.031 (2)	0.033 (2)	0.056 (3)	0.0105 (19)	−0.002 (2)	−0.015 (2)
C17	0.024 (2)	0.0231 (18)	0.038 (2)	−0.0027 (15)	0.0127 (17)	−0.0030 (16)
C18	0.040 (3)	0.028 (2)	0.037 (2)	0.0070 (18)	0.0044 (19)	−0.0044 (17)
C19	0.038 (3)	0.029 (2)	0.042 (2)	0.0114 (18)	0.005 (2)	−0.0021 (18)
C20	0.023 (2)	0.0228 (18)	0.042 (2)	−0.0019 (16)	0.0107 (17)	−0.0037 (16)
C21	0.053 (3)	0.047 (3)	0.030 (2)	0.016 (2)	0.009 (2)	0.0023 (19)
C22	0.026 (2)	0.0246 (19)	0.030 (2)	0.0004 (15)	0.0079 (16)	−0.0058 (15)
C23	0.028 (2)	0.0220 (18)	0.0293 (19)	−0.0055 (16)	0.0091 (16)	−0.0061 (15)
C24	0.056 (3)	0.037 (2)	0.037 (2)	0.018 (2)	0.003 (2)	0.001 (2)

Geometric parameters (Å, º)

O1—C5	1.220 (5)	C8—H8	0.9500
O2—C3	1.203 (5)	C9—C10	1.404 (6)
O3—C3	1.324 (5)	C9—C12	1.433 (5)
O3—C4	1.455 (5)	C10—C11	1.390 (5)
O4—C20	1.241 (5)	C10—H10	0.9500
O5—C23	1.198 (4)	C11—H11	0.9500
O6—C23	1.338 (4)	C12—C13	1.198 (5)
O6—C24	1.446 (5)	C13—C14	1.435 (5)
N1—C5	1.345 (5)	C14—C19	1.384 (6)
N1—C2	1.457 (4)	C14—C15	1.398 (6)
N1—H1	0.886 (14)	C15—C16	1.387 (6)
N2—C20	1.337 (5)	C15—H15	0.9500
N2—C22	1.457 (5)	C16—C17	1.377 (6)
N2—H2	0.894 (14)	C16—H16	0.9500
C1—C2	1.514 (6)	C17—C18	1.386 (6)
C1—H1A	0.9800	C17—C20	1.499 (5)
C1—H1B	0.9800	C18—C19	1.390 (6)
C1—H1C	0.9800	C18—H18	0.9500
C2—C3	1.523 (5)	C19—H19	0.9500
C2—H2A	1.0000	C21—C22	1.513 (6)
C4—H4A	0.9800	C21—H21A	0.9800
C4—H4B	0.9800	C21—H21B	0.9800
C4—H4C	0.9800	C21—H21C	0.9800
C5—C6	1.499 (5)	C22—C23	1.505 (5)
C6—C7	1.384 (5)	C22—H22	1.0000
C6—C11	1.392 (6)	C24—H24A	0.9800
C7—C8	1.393 (5)	C24—H24B	0.9800
C7—H7	0.9500	C24—H24C	0.9800
C8—C9	1.383 (6)
C3—O3—C4	115.2 (3)	C10—C11—C6	120.5 (4)
C23—O6—C24	115.7 (3)	C10—C11—H11	119.8
C5—N1—C2	119.7 (3)	C6—C11—H11	119.8
C5—N1—H1	122 (2)	C13—C12—C9	179.4 (5)
C2—N1—H1	117 (2)	C12—C13—C14	178.1 (4)
C20—N2—C22	122.6 (3)	C19—C14—C15	119.2 (4)
C20—N2—H2	119 (3)	C19—C14—C13	120.9 (4)
C22—N2—H2	119 (3)	C15—C14—C13	119.9 (4)
C2—C1—H1A	109.5	C16—C15—C14	119.4 (4)
C2—C1—H1B	109.5	C16—C15—H15	120.3
H1A—C1—H1B	109.5	C14—C15—H15	120.3
C2—C1—H1C	109.5	C17—C16—C15	121.4 (4)
H1A—C1—H1C	109.5	C17—C16—H16	119.3
H1B—C1—H1C	109.5	C15—C16—H16	119.3
N1—C2—C1	111.9 (3)	C16—C17—C18	119.1 (4)
N1—C2—C3	113.2 (3)	C16—C17—C20	120.0 (4)
C1—C2—C3	110.0 (3)	C18—C17—C20	121.0 (4)
N1—C2—H2A	107.2	C17—C18—C19	120.2 (4)
C1—C2—H2A	107.2	C17—C18—H18	119.9
C3—C2—H2A	107.2	C19—C18—H18	119.9
O2—C3—O3	123.5 (4)	C14—C19—C18	120.6 (4)
O2—C3—C2	122.0 (3)	C14—C19—H19	119.7
O3—C3—C2	114.5 (3)	C18—C19—H19	119.7
O3—C4—H4A	109.5	O4—C20—N2	122.0 (3)
O3—C4—H4B	109.5	O4—C20—C17	121.6 (3)
H4A—C4—H4B	109.5	N2—C20—C17	116.4 (3)
O3—C4—H4C	109.5	C22—C21—H21A	109.5
H4A—C4—H4C	109.5	C22—C21—H21B	109.5
H4B—C4—H4C	109.5	H21A—C21—H21B	109.5
O1—C5—N1	121.8 (3)	C22—C21—H21C	109.5
O1—C5—C6	122.1 (4)	H21A—C21—H21C	109.5
N1—C5—C6	116.0 (3)	H21B—C21—H21C	109.5
C7—C6—C11	119.2 (3)	N2—C22—C23	112.7 (3)
C7—C6—C5	122.0 (4)	N2—C22—C21	112.0 (3)
C11—C6—C5	118.7 (3)	C23—C22—C21	111.2 (3)
C6—C7—C8	120.5 (4)	N2—C22—H22	106.8
C6—C7—H7	119.7	C23—C22—H22	106.8
C8—C7—H7	119.7	C21—C22—H22	106.8
C9—C8—C7	120.7 (4)	O5—C23—O6	123.2 (4)
C9—C8—H8	119.6	O5—C23—C22	125.0 (3)
C7—C8—H8	119.6	O6—C23—C22	111.6 (3)
C8—C9—C10	118.9 (4)	O6—C24—H24A	109.5
C8—C9—C12	120.9 (4)	O6—C24—H24B	109.5
C10—C9—C12	120.2 (4)	H24A—C24—H24B	109.5
C11—C10—C9	120.2 (4)	O6—C24—H24C	109.5
C11—C10—H10	119.9	H24A—C24—H24C	109.5
C9—C10—H10	119.9	H24B—C24—H24C	109.5
C5—N1—C2—C1	164.9 (3)	C19—C14—C15—C16	−1.2 (7)
C5—N1—C2—C3	−70.2 (4)	C13—C14—C15—C16	177.1 (4)
C4—O3—C3—O2	−2.1 (6)	C14—C15—C16—C17	−1.4 (7)
C4—O3—C3—C2	−179.7 (3)	C15—C16—C17—C18	3.1 (7)
N1—C2—C3—O2	162.9 (4)	C15—C16—C17—C20	−176.0 (4)
C1—C2—C3—O2	−71.1 (5)	C16—C17—C18—C19	−2.1 (6)
N1—C2—C3—O3	−19.4 (5)	C20—C17—C18—C19	177.0 (4)
C1—C2—C3—O3	106.5 (4)	C15—C14—C19—C18	2.2 (7)
C2—N1—C5—O1	−0.6 (5)	C13—C14—C19—C18	−176.1 (4)
C2—N1—C5—C6	−178.0 (3)	C17—C18—C19—C14	−0.6 (7)
O1—C5—C6—C7	−142.9 (4)	C22—N2—C20—O4	−3.3 (6)
N1—C5—C6—C7	34.5 (5)	C22—N2—C20—C17	178.3 (3)
O1—C5—C6—C11	35.5 (6)	C16—C17—C20—O4	−38.6 (6)
N1—C5—C6—C11	−147.1 (4)	C18—C17—C20—O4	142.3 (4)
C11—C6—C7—C8	0.2 (6)	C16—C17—C20—N2	139.8 (4)
C5—C6—C7—C8	178.5 (3)	C18—C17—C20—N2	−39.3 (5)
C6—C7—C8—C9	1.3 (6)	C20—N2—C22—C23	46.3 (5)
C7—C8—C9—C10	−1.2 (6)	C20—N2—C22—C21	−80.0 (5)
C7—C8—C9—C12	178.9 (4)	C24—O6—C23—O5	3.1 (5)
C8—C9—C10—C11	−0.3 (6)	C24—O6—C23—C22	179.1 (3)
C12—C9—C10—C11	179.6 (4)	N2—C22—C23—O5	−134.7 (4)
C9—C10—C11—C6	1.8 (6)	C21—C22—C23—O5	−7.9 (5)
C7—C6—C11—C10	−1.8 (6)	N2—C22—C23—O6	49.4 (4)
C5—C6—C11—C10	179.8 (4)	C21—C22—C23—O6	176.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.89 (1)	2.11 (2)	2.982 (4)	168 (3)
N2—H2···O4^ii	0.89 (1)	1.93 (2)	2.799 (4)	165 (5)
C1—H1C···O2^i	0.98	2.58	3.532 (6)	164
C4—H4B···O2^iii	0.98	2.36	3.340 (5)	176
C21—H21B···O6^iii	0.98	2.53	3.315 (5)	137
C22—H22···O5^ii	1.00	2.38	3.380 (5)	174
C24—H24B···O5^iv	0.98	2.46	3.394 (5)	158

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