4-Nitro­benzyl 3,4-bis­(acet­yloxy)-2-(4-meth­oxy­phen­yl)pyrrolidine-1-carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry

Dallasta Pedroso, S.; Caracelli, I.; Zukerman-Schpector, J.; Soto-Monsalve, M.; De Almeida Santos, R.H.; Correia, C.R.D.; Llanes Garcia, A.L.; Kwong, H.C.; Tiekink, E.R.T.

doi:10.1107/S2056989020007914

4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

S. Dallasta Pedroso, I. Caracelli, J. Zukerman-Schpector, M. Soto-Monsalve, R. H. De Almeida Santos, C. R. D. Correia, A. L. Llanes Garcia, H. C. Kwong and E. R. T. Tiekink

The title compound, containing a tetra-substituted pyrrolidine ring, has an N-bound (equatorial) 4-nitrophenyl)ethylcarboxylate group with an adjacent C-bound 4-methoxyphenyl (bisectional) and then two acetyloxy subtituents in equatorial and axial positions, respectively. The five-membered ring is twisted about the bond bearing the acetyloxy subtituents.

Keywords: crystal structure; pyrrolidine; Hirshfeld surface analysis; NCI plots; computational chemistry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989020007914/hb7923sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989020007914/hb7923Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989020007914/hb7923Isup3.cml Supplementary material

CCDC reference: 2009242

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.112
Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent Resd 1  C   Ueq(max) / Ueq(min) Range        3.3 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.15 Why ?
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C2          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

   2 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
   1 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR2014 (Burla et al., 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), MarvinSketch (ChemAxon, 2010) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate top

Crystal data top

C₂₃H₂₄N₂O₉	F(000) = 1984
M_r = 472.44	D_x = 1.376 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 23.6396 (5) Å	Cell parameters from 9984 reflections
b = 8.2906 (2) Å	θ = 2.6–25.4°
c = 24.7683 (5) Å	µ = 0.11 mm⁻¹
β = 110.013 (1)°	T = 293 K
V = 4561.13 (18) Å³	Irregular, colourless
Z = 8	0.40 × 0.36 × 0.18 mm

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.020
Radiation source: Enraf–Nonius FR590	θ_max = 25.4°, θ_min = 1.8°
non–profiled ω/2θ scans	h = −28→28
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→10
T_min = 0.686, T_max = 0.745	l = −29→29
22357 measured reflections	3 standard reflections every 120 min
4172 independent reflections	intensity decay: 2%
3646 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0475P)² + 5.1476P] where P = (F_o² + 2F_c²)/3
4172 reflections	(Δ/σ)_max = 0.001
310 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.41109 (7)	0.33440 (18)	0.82213 (6)	0.0313 (3)
H1	0.439778	0.265045	0.812398	0.038*
C2	0.35064 (7)	0.33405 (19)	0.77230 (7)	0.0336 (4)
H2	0.327740	0.430457	0.774943	0.040*
C3	0.31777 (7)	0.1856 (2)	0.78170 (7)	0.0378 (4)
H3	0.274273	0.192051	0.761254	0.045*
C4	0.33330 (7)	0.1864 (2)	0.84615 (7)	0.0403 (4)
H4A	0.304809	0.251133	0.857137	0.048*
H4B	0.333567	0.077780	0.860767	0.048*
C5	0.43296 (7)	0.20974 (18)	0.91863 (7)	0.0345 (4)
C6	0.53264 (8)	0.2143 (2)	0.98048 (8)	0.0528 (5)
H6A	0.542252	0.103154	0.974917	0.063*
H6B	0.516931	0.217441	1.011878	0.063*
C7	0.58827 (8)	0.3154 (2)	0.99508 (7)	0.0417 (4)
C8	0.64314 (9)	0.2417 (3)	1.02204 (9)	0.0565 (5)
H8	0.644787	0.130582	1.027501	0.068*
C9	0.69526 (9)	0.3306 (3)	1.04088 (10)	0.0645 (6)
H9	0.732107	0.280446	1.058971	0.077*
C10	0.69219 (8)	0.4939 (3)	1.03263 (8)	0.0528 (5)
C11	0.63872 (9)	0.5713 (3)	1.00515 (9)	0.0544 (5)
H11	0.637581	0.682263	0.999450	0.065*
C12	0.58661 (8)	0.4804 (2)	0.98615 (8)	0.0494 (5)
H12	0.550017	0.530722	0.967144	0.059*
C13	0.43684 (7)	0.50197 (18)	0.83547 (6)	0.0316 (3)
C14	0.40971 (7)	0.6175 (2)	0.85901 (7)	0.0372 (4)
H14	0.376437	0.589579	0.868927	0.045*
C15	0.43136 (8)	0.7731 (2)	0.86789 (8)	0.0412 (4)
H15	0.412718	0.849067	0.883778	0.049*
C16	0.48067 (8)	0.8167 (2)	0.85329 (8)	0.0438 (4)
C17	0.50828 (8)	0.7033 (2)	0.83008 (9)	0.0513 (5)
H17	0.541530	0.731489	0.820158	0.062*
C18	0.48621 (8)	0.5466 (2)	0.82156 (8)	0.0430 (4)
H18	0.505194	0.470334	0.806132	0.052*
C19	0.54992 (12)	1.0247 (3)	0.85250 (17)	0.1022 (11)
H19A	0.583775	0.962689	0.875791	0.153*
H19B	0.557073	1.137012	0.861793	0.153*
H19C	0.544479	1.008448	0.812661	0.153*
C20	0.31789 (8)	0.3956 (2)	0.67329 (7)	0.0412 (4)
C21	0.33733 (10)	0.4076 (3)	0.62226 (9)	0.0641 (6)
H21A	0.341021	0.301250	0.608472	0.096*
H21B	0.375514	0.461491	0.632865	0.096*
H21C	0.307975	0.467627	0.592548	0.096*
C22	0.31168 (8)	−0.0347 (2)	0.71859 (8)	0.0416 (4)
C23	0.34279 (10)	−0.1848 (2)	0.71099 (9)	0.0565 (5)
H23A	0.329284	−0.273887	0.728173	0.085*
H23B	0.385482	−0.171936	0.729165	0.085*
H23C	0.333649	−0.205264	0.670751	0.085*
N1	0.39393 (6)	0.25809 (16)	0.86773 (6)	0.0352 (3)
N2	0.74834 (9)	0.5888 (3)	1.05360 (8)	0.0727 (6)
O1	0.41991 (6)	0.12222 (15)	0.95189 (5)	0.0462 (3)
O2	0.48803 (5)	0.27396 (14)	0.92893 (5)	0.0394 (3)
O3	0.79605 (8)	0.5171 (3)	1.06567 (10)	0.1097 (8)
O4	0.74408 (9)	0.7331 (3)	1.05857 (8)	0.0893 (6)
O5	0.49776 (7)	0.97485 (16)	0.86316 (8)	0.0654 (4)
O6	0.36272 (5)	0.33834 (15)	0.71959 (5)	0.0410 (3)
O7	0.26983 (6)	0.4321 (2)	0.67504 (6)	0.0632 (4)
O8	0.34399 (5)	0.04280 (14)	0.76655 (5)	0.0441 (3)
O9	0.26372 (7)	0.0104 (2)	0.68714 (6)	0.0684 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0301 (8)	0.0308 (8)	0.0299 (8)	0.0021 (6)	0.0061 (6)	0.0014 (6)
C2	0.0311 (8)	0.0356 (8)	0.0303 (8)	0.0036 (6)	0.0057 (6)	−0.0026 (6)
C3	0.0270 (8)	0.0371 (9)	0.0431 (9)	0.0004 (6)	0.0039 (7)	−0.0050 (7)
C4	0.0319 (8)	0.0426 (9)	0.0435 (9)	−0.0059 (7)	0.0091 (7)	0.0002 (7)
C5	0.0390 (9)	0.0266 (7)	0.0342 (8)	0.0002 (6)	0.0075 (7)	0.0010 (7)
C6	0.0460 (10)	0.0521 (11)	0.0440 (10)	−0.0034 (9)	−0.0057 (8)	0.0169 (9)
C7	0.0402 (9)	0.0491 (10)	0.0295 (8)	−0.0012 (8)	0.0037 (7)	0.0018 (7)
C8	0.0469 (11)	0.0589 (12)	0.0545 (12)	0.0051 (9)	0.0055 (9)	0.0106 (10)
C9	0.0381 (10)	0.0846 (17)	0.0617 (13)	0.0065 (10)	0.0053 (9)	0.0104 (12)
C10	0.0394 (10)	0.0797 (15)	0.0384 (10)	−0.0140 (10)	0.0121 (8)	−0.0139 (10)
C11	0.0595 (12)	0.0502 (11)	0.0546 (12)	−0.0096 (9)	0.0207 (10)	−0.0123 (9)
C12	0.0407 (10)	0.0497 (11)	0.0518 (11)	0.0012 (8)	0.0082 (8)	−0.0019 (9)
C13	0.0315 (8)	0.0317 (8)	0.0264 (7)	−0.0002 (6)	0.0032 (6)	0.0023 (6)
C14	0.0380 (9)	0.0376 (9)	0.0369 (9)	−0.0017 (7)	0.0140 (7)	0.0002 (7)
C15	0.0452 (10)	0.0365 (9)	0.0411 (9)	0.0006 (7)	0.0139 (8)	−0.0052 (7)
C16	0.0407 (9)	0.0327 (9)	0.0521 (11)	−0.0051 (7)	0.0085 (8)	−0.0015 (8)
C17	0.0409 (10)	0.0440 (10)	0.0746 (14)	−0.0085 (8)	0.0269 (10)	−0.0028 (9)
C18	0.0395 (9)	0.0381 (9)	0.0541 (11)	0.0003 (7)	0.0195 (8)	−0.0042 (8)
C19	0.0737 (17)	0.0508 (14)	0.194 (4)	−0.0262 (13)	0.061 (2)	−0.0194 (18)
C20	0.0432 (10)	0.0369 (9)	0.0345 (9)	0.0017 (7)	0.0017 (7)	−0.0005 (7)
C21	0.0683 (14)	0.0829 (16)	0.0367 (10)	−0.0014 (12)	0.0123 (10)	0.0033 (10)
C22	0.0423 (10)	0.0399 (9)	0.0401 (9)	−0.0079 (7)	0.0110 (8)	−0.0029 (7)
C23	0.0630 (13)	0.0459 (11)	0.0595 (13)	−0.0002 (9)	0.0196 (10)	−0.0112 (9)
N1	0.0330 (7)	0.0341 (7)	0.0328 (7)	−0.0050 (6)	0.0042 (6)	0.0035 (6)
N2	0.0582 (12)	0.1074 (18)	0.0531 (11)	−0.0282 (12)	0.0200 (9)	−0.0212 (11)
O1	0.0504 (7)	0.0427 (7)	0.0422 (7)	−0.0020 (6)	0.0116 (6)	0.0132 (6)
O2	0.0364 (6)	0.0372 (6)	0.0338 (6)	−0.0042 (5)	−0.0019 (5)	0.0075 (5)
O3	0.0421 (10)	0.154 (2)	0.1255 (18)	−0.0190 (12)	0.0188 (10)	−0.0200 (15)
O4	0.0919 (13)	0.1010 (15)	0.0811 (13)	−0.0485 (12)	0.0372 (11)	−0.0322 (11)
O5	0.0564 (8)	0.0360 (7)	0.1062 (13)	−0.0139 (6)	0.0308 (8)	−0.0144 (7)
O6	0.0363 (6)	0.0518 (7)	0.0304 (6)	0.0068 (5)	0.0058 (5)	−0.0001 (5)
O7	0.0482 (8)	0.0815 (11)	0.0506 (8)	0.0230 (7)	0.0050 (6)	0.0112 (7)
O8	0.0352 (6)	0.0376 (6)	0.0502 (7)	0.0009 (5)	0.0024 (5)	−0.0093 (5)
O9	0.0561 (9)	0.0722 (10)	0.0559 (9)	0.0083 (8)	−0.0077 (7)	−0.0200 (8)

Geometric parameters (Å, º) top

C1—N1	1.468 (2)	C12—H12	0.9300
C1—C13	1.507 (2)	C13—C18	1.376 (2)
C1—C2	1.536 (2)	C13—C14	1.388 (2)
C1—H1	0.9800	C14—C15	1.377 (2)
C2—O6	1.4293 (19)	C14—H14	0.9300
C2—C3	1.516 (2)	C15—C16	1.381 (3)
C2—H2	0.9800	C15—H15	0.9300
C3—O8	1.444 (2)	C16—O5	1.369 (2)
C3—C4	1.511 (2)	C16—C17	1.378 (3)
C3—H3	0.9800	C17—C18	1.388 (3)
C4—N1	1.472 (2)	C17—H17	0.9300
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—O5	1.409 (3)
C5—O1	1.214 (2)	C19—H19A	0.9600
C5—N1	1.344 (2)	C19—H19B	0.9600
C5—O2	1.3476 (19)	C19—H19C	0.9600
C6—O2	1.4371 (19)	C20—O7	1.191 (2)
C6—C7	1.496 (3)	C20—O6	1.354 (2)
C6—H6A	0.9700	C20—C21	1.488 (3)
C6—H6B	0.9700	C21—H21A	0.9600
C7—C8	1.382 (3)	C21—H21B	0.9600
C7—C12	1.385 (3)	C21—H21C	0.9600
C8—C9	1.373 (3)	C22—O9	1.195 (2)
C8—H8	0.9300	C22—O8	1.337 (2)
C9—C10	1.368 (3)	C22—C23	1.490 (3)
C9—H9	0.9300	C23—H23A	0.9600
C10—C11	1.372 (3)	C23—H23B	0.9600
C10—N2	1.476 (3)	C23—H23C	0.9600
C11—C12	1.382 (3)	N2—O3	1.218 (3)
C11—H11	0.9300	N2—O4	1.210 (3)

N1—C1—C13	115.20 (13)	C18—C13—C1	120.44 (15)
N1—C1—C2	101.03 (12)	C14—C13—C1	121.24 (14)
C13—C1—C2	111.89 (12)	C15—C14—C13	120.91 (16)
N1—C1—H1	109.5	C15—C14—H14	119.5
C13—C1—H1	109.5	C13—C14—H14	119.5
C2—C1—H1	109.5	C14—C15—C16	120.28 (16)
O6—C2—C3	115.70 (13)	C14—C15—H15	119.9
O6—C2—C1	108.19 (12)	C16—C15—H15	119.9
C3—C2—C1	105.25 (13)	O5—C16—C17	125.10 (17)
O6—C2—H2	109.2	O5—C16—C15	115.33 (17)
C3—C2—H2	109.2	C17—C16—C15	119.56 (16)
C1—C2—H2	109.2	C16—C17—C18	119.65 (17)
O8—C3—C4	107.94 (14)	C16—C17—H17	120.2
O8—C3—C2	109.73 (13)	C18—C17—H17	120.2
C4—C3—C2	101.92 (13)	C13—C18—C17	121.37 (17)
O8—C3—H3	112.2	C13—C18—H18	119.3
C4—C3—H3	112.2	C17—C18—H18	119.3
C2—C3—H3	112.2	O5—C19—H19A	109.5
N1—C4—C3	103.88 (13)	O5—C19—H19B	109.5
N1—C4—H4A	111.0	H19A—C19—H19B	109.5
C3—C4—H4A	111.0	O5—C19—H19C	109.5
N1—C4—H4B	111.0	H19A—C19—H19C	109.5
C3—C4—H4B	111.0	H19B—C19—H19C	109.5
H4A—C4—H4B	109.0	O7—C20—O6	122.57 (17)
O1—C5—N1	124.23 (15)	O7—C20—C21	126.14 (17)
O1—C5—O2	124.12 (15)	O6—C20—C21	111.29 (16)
N1—C5—O2	111.62 (14)	C20—C21—H21A	109.5
O2—C6—C7	109.81 (15)	C20—C21—H21B	109.5
O2—C6—H6A	109.7	H21A—C21—H21B	109.5
C7—C6—H6A	109.7	C20—C21—H21C	109.5
O2—C6—H6B	109.7	H21A—C21—H21C	109.5
C7—C6—H6B	109.7	H21B—C21—H21C	109.5
H6A—C6—H6B	108.2	O9—C22—O8	123.71 (17)
C8—C7—C12	119.00 (18)	O9—C22—C23	125.35 (17)
C8—C7—C6	118.12 (17)	O8—C22—C23	110.92 (15)
C12—C7—C6	122.73 (17)	C22—C23—H23A	109.5
C9—C8—C7	120.8 (2)	C22—C23—H23B	109.5
C9—C8—H8	119.6	H23A—C23—H23B	109.5
C7—C8—H8	119.6	C22—C23—H23C	109.5
C10—C9—C8	119.0 (2)	H23A—C23—H23C	109.5
C10—C9—H9	120.5	H23B—C23—H23C	109.5
C8—C9—H9	120.5	C5—N1—C1	124.66 (13)
C9—C10—C11	121.97 (19)	C5—N1—C4	119.39 (14)
C9—C10—N2	118.7 (2)	C1—N1—C4	112.69 (12)
C11—C10—N2	119.3 (2)	O3—N2—O4	124.1 (2)
C10—C11—C12	118.5 (2)	O3—N2—C10	118.1 (2)
C10—C11—H11	120.8	O4—N2—C10	117.8 (2)
C12—C11—H11	120.8	C5—O2—C6	113.56 (13)
C11—C12—C7	120.73 (18)	C16—O5—C19	118.13 (17)
C11—C12—H12	119.6	C20—O6—C2	116.07 (13)
C7—C12—H12	119.6	C22—O8—C3	117.36 (13)
C18—C13—C14	118.23 (15)

N1—C1—C2—O6	−155.47 (12)	C15—C16—C17—C18	0.1 (3)
C13—C1—C2—O6	81.46 (16)	C14—C13—C18—C17	−0.7 (3)
N1—C1—C2—C3	−31.22 (15)	C1—C13—C18—C17	175.80 (16)
C13—C1—C2—C3	−154.29 (13)	C16—C17—C18—C13	0.5 (3)
O6—C2—C3—O8	44.85 (17)	O1—C5—N1—C1	−166.43 (16)
C1—C2—C3—O8	−74.51 (15)	O2—C5—N1—C1	15.2 (2)
O6—C2—C3—C4	159.06 (13)	O1—C5—N1—C4	−8.4 (3)
C1—C2—C3—C4	39.70 (16)	O2—C5—N1—C4	173.30 (14)
O8—C3—C4—N1	83.80 (15)	C13—C1—N1—C5	−68.82 (19)
C2—C3—C4—N1	−31.73 (16)	C2—C1—N1—C5	170.43 (14)
O2—C6—C7—C8	−148.04 (18)	C13—C1—N1—C4	131.85 (14)
O2—C6—C7—C12	36.3 (3)	C2—C1—N1—C4	11.10 (16)
C12—C7—C8—C9	1.3 (3)	C3—C4—N1—C5	−147.44 (15)
C6—C7—C8—C9	−174.4 (2)	C3—C4—N1—C1	13.09 (18)
C7—C8—C9—C10	0.1 (3)	C9—C10—N2—O3	16.0 (3)
C8—C9—C10—C11	−1.2 (3)	C11—C10—N2—O3	−163.5 (2)
C8—C9—C10—N2	179.30 (19)	C9—C10—N2—O4	−162.9 (2)
C9—C10—C11—C12	0.9 (3)	C11—C10—N2—O4	17.7 (3)
N2—C10—C11—C12	−179.61 (18)	O1—C5—O2—C6	7.0 (2)
C10—C11—C12—C7	0.6 (3)	N1—C5—O2—C6	−174.71 (15)
C8—C7—C12—C11	−1.7 (3)	C7—C6—O2—C5	−168.20 (15)
C6—C7—C12—C11	173.92 (19)	C17—C16—O5—C19	−4.5 (3)
N1—C1—C13—C18	137.44 (16)	C15—C16—O5—C19	176.2 (2)
C2—C1—C13—C18	−107.93 (17)	O7—C20—O6—C2	−4.1 (2)
N1—C1—C13—C14	−46.17 (19)	C21—C20—O6—C2	175.16 (15)
C2—C1—C13—C14	68.47 (19)	C3—C2—O6—C20	85.09 (17)
C18—C13—C14—C15	0.4 (2)	C1—C2—O6—C20	−157.16 (13)
C1—C13—C14—C15	−176.07 (15)	O9—C22—O8—C3	2.4 (3)
C13—C14—C15—C16	0.1 (3)	C23—C22—O8—C3	−176.13 (15)
C14—C15—C16—O5	179.04 (16)	C4—C3—O8—C22	141.18 (15)
C14—C15—C16—C17	−0.4 (3)	C2—C3—O8—C22	−108.54 (16)
O5—C16—C17—C18	−179.27 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O7ⁱ	0.97	2.60	3.129 (2)	115
C6—H6A···O1ⁱⁱ	0.97	2.54	3.250 (2)	130

Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+2.

Summary of short interatomic contacts (Å) in (I)^a top

Contact	Distance	Symmetry operation
C6—H6A···O1^b	2.47	-x + 1, -y, -z + 2
C4—H4B···O7^b	2.55	-x + 1/2, y - 1/2, -z + 3/2
C4···O7	3.13	-x + 1/2, y + 1/2, -z + 3/2
C5···O5	3.08	x, y - 1, z
O2···O5	3.02	x, y - 1, z
C6—H6B···C15	2.73	-x + 1, -y + 1, -z + 2
C9—H9···C21	2.75	x + 1/2, -y + 1/2, z + 1/2
O4···O4	2.75	-x + 3/2, -y + 3/2, -z + 2
H17···H23B	2.35	-x + 1, y + 1, -z + 3/2

Notes: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al., 2017) whereby the X—H bond lengths are adjusted to their neutron values. (b) These interactions correspond to the interactions listed in Table 1.

Percentage contributions of interatomic contacts to the Hirshfeld surface for (I) top

Contact	Percentage contribution
H···H	42.3
H···O/O···H	37.3
H···C/C···H	14.9
O···O	2.1
O···C/C···O	1.2
Others	2.2

Summary of interaction energies (kJ mol^-1) calculated for (I). top

Contact	R (Å)	E_ele	E_pol	E_dis	E_rep	E_tot
Intra-layer region
C4—H4B···O7ⁱ +
C4···O7ⁱ	10.99	-17.8	-6.1	-29.1	18.3	-37.3
C6—H6A···O1ⁱⁱ	9.21	-23.8	-6.9	-23.2	21.7	-37.0
C5···O5ⁱⁱⁱ +
O2···O5ⁱⁱⁱ	8.29	-8.4	-2.7	-56.3	29.1	-41.8
C9—H9···C21^iv	14.12	-12.7	-3.4	-20.5	12.0	-26.4
C6—H6B···C15^v +
C4—H4A···O4^v	6.55	-18.1	-4.5	-87.1	52.8	-65.8
C21—H21C···O4^vi	15.04	-2.1	-1.0	-3.7	1.5	-5.2
Inter-layer region
H17···H23B^vii	10.38	2.9	-1.2	-16.5	8.2	-7.1
H17···H21B^vii +
H18···H21B^viii	6.24	-1.1	-1.6	-52.9	23.0	-34.2
O4···O4^ix	13.71	-16.1	-4.4	-16.2	10.8	-27.7
C8—H8···O3^x	12.70	-5.4	-1.3	-10.2	1.9	-14.4

Symmetry codes: (i) -x + 1/2, y - 1/2, -z + 3/2; (ii) -x + 1, -y, -z + 2; (iii) x, y - 1, z; (iv) x + 1/2, -y + 1/2, z + 1/2; (v) -x + 1, -y + 1, -z + 2; (vi) x - 1/2, -y + 3/2, z - 1/2; (vii) -x + 1, y + 1, - z + 3/2; (viii) -x + 1, y, -z + 3/2; (ix) -x + 3/2, -y + 3/2, -z + 2; (x) -x + 3/2, -y + 1/2, -z + 2.

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4-Nitro­benzyl 3,4-bis­(acet­yloxy)-2-(4-meth­oxy­phen­yl)pyrrolidine-1-carboxyl­ate: crystal structure, Hirshfeld surface analysis and computational chemistry

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4-Nitrobenzyl 3,4-bis(acetyloxy)-2-(4-methoxyphenyl)pyrrolidine-1-carboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry