(2R*,3R*,4R*)-tert-Butyl 2-(diethoxy­phosphor­yl)-4-nitro-3-(4-nitro­phen­yl)penta­noate

The title compound, C₁₉H₂₉N₂O₉P, was isolated as a single diastereoisomer. The mol­ecule adopts an extended conformation with the phosphoryl and 4-nitro­phenyl groups placed in anti­periplanar positions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.072
• wR factor = 0.207
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.62 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.15 Ratio
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C1     -   C2     ...       1.26 Ang.

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.61
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) ...       3.19 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C1      ..       5.85 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C3      ..       6.18 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Bruker, 2003); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(2R*,3R*,4R*)-tert-Butyl 2-(diethoxyphosphoryl)-4-nitro-3-(4-nitrophenyl)pentanoate

Crystal data

C19H29N2O9P	Dx = 1.290 Mg m^−3
Mr = 460.41	Melting point: 216 K
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 12.3654 (4) Å	Cell parameters from 8454 reflections
b = 9.7216 (3) Å	θ = 3.8–70.6°
c = 20.4966 (7) Å	µ = 1.47 mm^−1
β = 105.814 (2)°	T = 293 K
V = 2370.67 (13) Å^3	Prism, colorless
Z = 4	0.16 × 0.13 × 0.10 mm
F(000) = 976

Data collection

Bruker SMART APEX diffractometer	4506 independent reflections
Radiation source: fine-focus sealed tube	4262 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scans	θmax = 70.7°, θmin = 3.7°
Absorption correction: multi-scan (SHELXTL; Bruker, 2003)	h = −15→15
Tmin = 0.776, Tmax = 0.867	k = −11→11
25754 measured reflections	l = −24→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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.1223P)^2 + 1.8058P] where P = (Fo^2 + 2Fc^2)/3
4506 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.97 e Å^−3
12 restraints	Δρmin = −0.37 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
P	0.63908 (6)	0.34199 (8)	0.39588 (4)	0.0649 (3)
O1	0.5608 (2)	0.2284 (3)	0.39369 (13)	0.0849 (7)
O2	0.6004 (3)	0.4533 (3)	0.33993 (12)	0.1016 (9)
O3	0.75591 (19)	0.3036 (3)	0.38856 (12)	0.0775 (6)
O4	0.56859 (17)	0.3514 (2)	0.55225 (13)	0.0737 (6)
O5	0.73483 (15)	0.26392 (19)	0.54665 (9)	0.0565 (5)
O6	0.9669 (2)	0.6362 (3)	0.46242 (16)	0.0929 (8)
O7	0.8968 (3)	0.8265 (3)	0.4806 (2)	0.1172 (11)
O8	0.9270 (4)	0.7668 (6)	0.79633 (19)	0.179 (2)
O9	0.7565 (3)	0.8017 (6)	0.77714 (17)	0.1522 (16)
N1	0.8883 (2)	0.7067 (3)	0.46270 (13)	0.0657 (6)
N2	0.8353 (3)	0.7618 (5)	0.75961 (15)	0.1066 (12)
C1	0.5544 (6)	0.4283 (9)	0.2725 (3)	0.157 (3)
H11	0.622	0.4379	0.2482	0.189*
H12	0.5289	0.320	0.2681	0.189*
C2	0.4728 (6)	0.4958 (10)	0.2369 (3)	0.174 (3)
H21	0.4436	0.5549	0.2656	0.191*
H22	0.4150	0.4336	0.2133	0.191*
H23	0.4975	0.5504	0.2047	0.191*
C3	0.8076 (3)	0.1646 (4)	0.4083 (2)	0.0864 (10)
H31	0.8637	0.1713	0.4502	0.104*
H32	0.7518	0.103	0.4140	0.104*
C4	0.8568 (4)	0.1132 (6)	0.3569 (3)	0.1165 (16)
H41	0.7998	0.1069	0.3145	0.140*
H42	0.8883	0.0238	0.3698	0.140*
H43	0.9149	0.1748	0.3522	0.140*
C5	0.6585 (2)	0.4450 (3)	0.47229 (13)	0.0523 (6)
H51	0.591 (3)	0.503 (3)	0.4608 (15)	0.063 (8)*
C6	0.6463 (2)	0.3489 (3)	0.52825 (14)	0.0535 (6)
C7	0.7393 (3)	0.1569 (3)	0.59935 (18)	0.0716 (8)
C8	0.6374 (4)	0.0651 (4)	0.5775 (3)	0.1064 (15)
H81	0.6465	−0.0126	0.6074	0.128*
H82	0.6292	0.0338	0.5320	0.128*
H83	0.5716	0.1158	0.5793	0.128*
C9	0.7509 (4)	0.2284 (6)	0.6661 (2)	0.1048 (14)
H91	0.6821	0.2753	0.6650	0.126*
H92	0.8112	0.2938	0.6739	0.126*
H93	0.7667	0.1617	0.7020	0.126*
C10	0.8464 (3)	0.0793 (5)	0.5997 (2)	0.1007 (14)
H101	0.9085	0.1423	0.6088	0.121*
H102	0.8380	0.0368	0.5563	0.121*
H103	0.8604	0.0098	0.6343	0.121*
C11	0.7679 (2)	0.5308 (3)	0.49427 (12)	0.0489 (5)
H111	0.828 (2)	0.465 (3)	0.4947 (15)	0.062 (8)*
C12	0.7732 (2)	0.6419 (3)	0.44067 (14)	0.0547 (6)
H121	0.774 (2)	0.599 (3)	0.4039 (14)	0.046 (7)*
C13	0.6833 (3)	0.7520 (3)	0.42720 (17)	0.0716 (8)
H131	0.6109	0.7104	0.4092	0.086*
H132	0.6970	0.8170	0.3951	0.086*
H133	0.6851	0.7985	0.4688	0.086*
C14	0.7832 (2)	0.5922 (3)	0.56458 (12)	0.0480 (5)
C15	0.6953 (2)	0.6554 (3)	0.58360 (13)	0.0529 (6)
H15	0.631	0.6603	0.5555	0.063*
C16	0.7113 (2)	0.7100 (3)	0.64756 (14)	0.0583 (6)
H16	0.653	0.7509	0.6600	0.070*
C17	0.8165 (3)	0.7013 (3)	0.69222 (14)	0.0655 (7)
C18	0.9049 (3)	0.6387 (4)	0.67572 (16)	0.0775 (9)
H18	0.969	0.6335	0.7042	0.093*
C19	0.8872 (2)	0.5843 (4)	0.61123 (14)	0.0644 (7)
H19	0.948	0.5405	0.5988	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.0622 (5)	0.0674 (5)	0.0606 (5)	0.0038 (3)	0.0093 (3)	−0.0117 (3)
O1	0.0705 (13)	0.0852 (16)	0.0948 (17)	−0.0117 (12)	0.0152 (12)	−0.0303 (13)
O2	0.127 (2)	0.0950 (18)	0.0613 (13)	0.0110 (16)	−0.0119 (13)	−0.0062 (13)
O3	0.0771 (14)	0.0853 (15)	0.0785 (14)	−0.0060 (12)	0.0356 (11)	−0.0162 (12)
O4	0.0586 (11)	0.0698 (13)	0.1032 (16)	0.0118 (9)	0.0398 (11)	0.0146 (11)
O5	0.0524 (10)	0.0571 (10)	0.0623 (10)	0.0072 (8)	0.0194 (8)	0.0070 (8)
O6	0.0660 (14)	0.0963 (18)	0.123 (2)	0.0117 (13)	0.0370 (14)	0.0096 (16)
O7	0.095 (2)	0.0803 (19)	0.176 (3)	−0.0143 (15)	0.036 (2)	−0.0227 (19)
O8	0.143 (3)	0.275 (5)	0.090 (2)	0.048 (3)	−0.020 (2)	−0.078 (3)
O9	0.145 (3)	0.234 (4)	0.0802 (19)	0.029 (3)	0.0362 (19)	−0.058 (2)
N1	0.0647 (14)	0.0695 (16)	0.0687 (15)	−0.0018 (12)	0.0279 (12)	0.0085 (12)
N2	0.113 (2)	0.150 (3)	0.0520 (15)	0.022 (2)	0.0128 (16)	−0.0250 (18)
C1	0.185 (6)	0.176 (6)	0.085 (3)	0.012 (5)	−0.008 (4)	0.010 (4)
C2	0.187 (6)	0.213 (8)	0.083 (3)	0.036 (6)	−0.027 (4)	0.028 (4)
C3	0.082 (2)	0.090 (3)	0.090 (2)	0.0181 (19)	0.0264 (19)	−0.0005 (19)
C4	0.119 (4)	0.108 (3)	0.139 (4)	0.032 (3)	0.065 (3)	−0.005 (3)
C5	0.0452 (12)	0.0541 (14)	0.0560 (14)	0.0086 (10)	0.0115 (10)	−0.0008 (11)
C6	0.0507 (13)	0.0466 (13)	0.0636 (15)	0.0026 (10)	0.0164 (11)	−0.0012 (11)
C7	0.0689 (18)	0.0663 (18)	0.083 (2)	0.0145 (14)	0.0264 (16)	0.0233 (15)
C8	0.096 (3)	0.061 (2)	0.169 (4)	−0.0017 (19)	0.048 (3)	0.027 (2)
C9	0.122 (3)	0.124 (4)	0.074 (2)	0.019 (3)	0.038 (2)	0.024 (2)
C10	0.091 (3)	0.097 (3)	0.119 (3)	0.042 (2)	0.038 (2)	0.039 (2)
C11	0.0481 (12)	0.0506 (13)	0.0501 (13)	0.0037 (10)	0.0170 (10)	−0.0019 (10)
C12	0.0587 (15)	0.0615 (15)	0.0474 (13)	0.0020 (12)	0.0205 (11)	0.0006 (12)
C13	0.081 (2)	0.0691 (18)	0.0700 (18)	0.0155 (15)	0.0285 (15)	0.0203 (15)
C14	0.0528 (13)	0.0469 (12)	0.0473 (12)	0.0014 (10)	0.0189 (10)	0.0015 (10)
C15	0.0494 (13)	0.0597 (15)	0.0506 (13)	0.0024 (11)	0.0154 (11)	0.0006 (11)
C16	0.0659 (16)	0.0601 (15)	0.0551 (14)	0.0045 (13)	0.0272 (12)	−0.0016 (12)
C17	0.0802 (19)	0.0708 (18)	0.0464 (14)	0.0023 (15)	0.0184 (13)	−0.0037 (13)
C18	0.0654 (18)	0.102 (3)	0.0571 (16)	0.0133 (17)	0.0033 (13)	−0.0063 (16)
C19	0.0550 (14)	0.0798 (19)	0.0581 (15)	0.0114 (14)	0.0147 (12)	−0.0045 (14)

Geometric parameters (Å, º)

P—O1	1.461 (3)	C17—C18	1.372 (5)
P—O2	1.554 (3)	C18—C19	1.385 (4)
P—O3	1.538 (2)	C1—H11	1.09
P—C5	1.819 (3)	C1—H12	1.09
O2—C1	1.365 (6)	C2—H21	0.96
O3—C3	1.503 (5)	C2—H22	0.96
N1—C12	1.509 (4)	C2—H23	0.96
N2—C17	1.460 (4)	C3—H31	0.95
C1—C2	1.256 (8)	C3—H32	0.95
C3—C4	1.442 (6)	C4—H41	0.96
O4—C6	1.194 (3)	C4—H42	0.96
O5—C6	1.340 (3)	C4—H43	0.96
O5—C7	1.490 (3)	C5—H51	0.98 (3)
O6—N1	1.190 (3)	C8—H81	0.96
O7—N1	1.216 (4)	C8—H82	0.96
O8—N2	1.178 (5)	C8—H83	0.96
O9—N2	1.191 (5)	C9—H91	0.96
N1—C12	1.509 (4)	C9—H92	0.96
N2—C17	1.460 (4)	C9—H93	0.96
C5—C6	1.518 (4)	C10—H101	0.96
C7—C9	1.506 (6)	C10—H102	0.96
C7—C8	1.509 (5)	C10—H103	0.96
C7—C10	1.523 (5)	C11—H111	0.98 (3)
C5—C11	1.549 (4)	C12—H121	0.86 (3)
C11—C14	1.523 (3)	C13—H131	0.96
C11—C12	1.555 (4)	C13—H132	0.96
C14—C19	1.380 (4)	C13—H133	0.96
C14—C15	1.394 (3)	C15—H15	0.84
C15—C16	1.378 (4)	C16—H16	0.91
C12—C13	1.513 (4)	C18—H18	0.84
C16—C17	1.374 (4)	C19—H19	0.96
O1—P—O2	115.82 (16)	C7—C8—H81	109.5
O1—P—O3	116.47 (14)	C7—C8—H82	109.5
O1—P—C5	111.91 (14)	H81—C8—H82	109.5
O2—P—C5	101.19 (14)	C7—C8—H83	109.5
O3—P—O2	101.82 (16)	H81—C8—H83	109.5
O3—P—C5	108.10 (12)	H82—C8—H83	109.5
C1—O2—P	125.6 (4)	C7—C9—H91	109.5
C3—O3—P	122.2 (2)	C7—C9—H92	109.5
C6—O5—C7	120.0 (2)	H91—C9—H92	109.5
O6—N1—O7	123.3 (3)	C7—C9—H93	109.5
O6—N1—C12	117.5 (3)	H91—C9—H93	109.5
O7—N1—C12	119.1 (3)	H92—C9—H93	109.5
O8—N2—O9	121.1 (4)	C7—C10—H101	109.5
O8—N2—C17	119.9 (4)	C7—C10—H102	109.5
O9—N2—C17	119.0 (4)	H101—C10—H102	109.5
C2—C1—O2	122.8 (7)	C7—C10—H103	109.5
C2—C1—H11	106.6	H101—C10—H103	109.5
O2—C1—H11	106.6	H102—C10—H103	109.5
C2—C1—H12	106.6	C14—C11—C5	111.07 (19)
O2—C1—H12	106.6	C14—C11—C12	112.2 (2)
H11—C1—H12	106.6	C5—C11—C12	111.7 (2)
C1—C2—H21	109.5	C14—C11—H111	110.4 (18)
C1—C2—H22	109.5	C5—C11—H111	104.6 (18)
H21—C2—H22	109.5	C12—C11—H111	106.4 (18)
C1—C2—H23	109.5	N1—C12—C13	110.2 (3)
H21—C2—H23	109.5	N1—C12—C11	107.3 (2)
H22—C2—H23	109.5	C13—C12—C11	116.8 (2)
C4—C3—O3	110.3 (4)	N1—C12—H121	103.2 (17)
C4—C3—H31	109.6	C13—C12—H121	111.4 (18)
O3—C3—H31	109.6	C11—C12—H121	107.1 (18)
C4—C3—H32	109.6	C12—C13—H131	109.5
O3—C3—H32	109.6	C12—C13—H132	109.5
H31—C3—H32	108.1	H131—C13—H132	109.5
C3—C4—H41	109.5	C12—C13—H133	109.5
C3—C4—H42	109.5	H131—C13—H133	109.5
H41—C4—H42	109.5	H132—C13—H133	109.5
C3—C4—H43	109.5	C19—C14—C15	118.8 (2)
H41—C4—H43	109.5	C19—C14—C11	119.1 (2)
H42—C4—H43	109.5	C15—C14—C11	122.2 (2)
C6—C5—C11	111.7 (2)	C16—C15—C14	121.0 (3)
C6—C5—P	107.15 (18)	C16—C15—H15	119.5
C11—C5—P	116.52 (17)	C14—C15—H15	119.5
C6—C5—H51	106.5 (18)	C17—C16—C15	118.3 (3)
C11—C5—H51	112.2 (18)	C17—C16—H16	120.8
P—C5—H51	101.9 (18)	C15—C16—H16	120.8
O4—C6—O5	125.8 (3)	C18—C17—C16	122.4 (3)
O4—C6—C5	123.7 (2)	C18—C17—N2	118.7 (3)
O5—C6—C5	110.5 (2)	C16—C17—N2	118.9 (3)
O5—C7—C9	108.2 (3)	C17—C18—C19	118.4 (3)
O5—C7—C8	109.6 (3)	C17—C18—H18	120.8
C9—C7—C8	114.0 (3)	C19—C18—H18	120.8
O5—C7—C10	102.1 (3)	C14—C19—C18	121.0 (3)
C9—C7—C10	110.9 (3)	C14—C19—H19	119.5
C8—C7—C10	111.3 (3)	C18—C19—H19	119.5
O1—P—C5—C11	157.8 (2)	C6—O5—C7—C10	175.6 (3)
P—C5—C11—C12	63.5 (3)	C6—C5—C11—C14	−46.7 (3)
P—C5—C11—C14	−170.33 (17)	C6—C5—C11—C12	−172.9 (2)
N1—C12—C11—C5	−173.1 (2)	O6—N1—C12—C13	−165.8 (3)
N1—C12—C11—C14	61.4 (3)	O7—N1—C12—C13	15.2 (4)
C13—C12—C11—C14	−62.7 (3)	O6—N1—C12—C11	66.2 (3)
O1—P—O2—C1	−45.8 (5)	O7—N1—C12—C11	−112.9 (3)
O3—P—O2—C1	81.5 (5)	C5—C11—C12—C13	62.8 (3)
C5—P—O2—C1	−167.1 (5)	C5—C11—C14—C19	134.6 (3)
O1—P—O3—C3	−26.2 (3)	C12—C11—C14—C19	−99.5 (3)
O2—P—O3—C3	−153.1 (3)	C5—C11—C14—C15	−44.9 (3)
C5—P—O3—C3	100.8 (3)	C12—C11—C14—C15	80.9 (3)
P—O2—C1—C2	138.7 (7)	C19—C14—C15—C16	0.3 (4)
P—O3—C3—C4	135.3 (3)	C11—C14—C15—C16	179.9 (2)
O1—P—C5—C6	31.9 (2)	C14—C15—C16—C17	0.4 (4)
O3—P—C5—C6	−97.69 (19)	C15—C16—C17—C18	−1.1 (5)
O2—P—C5—C6	155.8 (2)	C15—C16—C17—N2	178.5 (3)
O3—P—C5—C11	28.2 (2)	O8—N2—C17—C18	6.6 (7)
O2—P—C5—C11	−78.3 (2)	O9—N2—C17—C18	−171.2 (5)
C7—O5—C6—O4	2.8 (4)	O8—N2—C17—C16	−173.0 (5)
C7—O5—C6—C5	−177.9 (2)	O9—N2—C17—C16	9.2 (7)
C11—C5—C6—O4	121.3 (3)	C16—C17—C18—C19	1.0 (6)
P—C5—C6—O4	−109.9 (3)	N2—C17—C18—C19	−178.6 (4)
C11—C5—C6—O5	−58.0 (3)	C15—C14—C19—C18	−0.4 (5)
P—C5—C6—O5	70.8 (2)	C11—C14—C19—C18	−180.0 (3)
C6—O5—C7—C9	−67.4 (4)	C17—C18—C19—C14	−0.3 (6)
C6—O5—C7—C8	57.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H51···O4^i	0.98 (3)	2.38 (4)	3.360 (3)	173 (2)
C16—H16···O1^i	0.91	2.58	3.293 (4)	135
C19—H19···O6^ii	0.96	2.52	3.408 (4)	154

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