(E)-N-Phenyl-N-(phenyl­carbamo­yl)-3-[prop­yl(tri­methyl­sil­yl)amino]­acryl­amide chloro­form hemisolvate

Herbig, M.; Böhme, U.

doi:10.1107/S2414314623001177

(E)-N-Phenyl-N-(phenylcarbamoyl)-3-[propyl(trimethylsilyl)amino]acrylamide chloroform hemisolvate

The title compound, C₂₂H₂₉N₃O₂Si·0.5CHCl₃, crystallizes in the the triclinic space group P $\overline{1}$ with two host molecules and one chloroform molecule in the asymmetric unit. The core of the molecule consists of a urea unit bound to a 3-amino-acryloyl group. These units are almost planar in both molecules [average deviation from plane of 0.05 (6) Å in molecule A and 0.04 (5) Å in molecule B]. The main difference between molecules A and B involves the dihedral angles of the phenyl groups. One phenyl ring makes dihedral angles of 71.14 (6)° (molecule A) and 82.81 (7)° (molecule B) with respect to the core (C₄N₃O₂) of the molecule [14.56 (9)° (molecule A) and 5.7 (1)° (molecule B) for the other phenyl ring]. Another prominent feature is the intramolecular N—H

O hydrogen bond present in both crystallographically independent molecules.

Keywords: crystal structure; organosilane; phenyl isocyanate; insertion.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314623001177/im4017sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314623001177/im4017Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314623001177/im4017Isup3.cml Supplementary material

CCDC reference: 2240673

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.055
wR factor = 0.123
Data-to-parameter ratio = 18.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 2  C   Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        5.7 Ratio
PLAT260_ALERT_2_C Large Average Ueq of Residue Including      Cl1B      0.111 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.457 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          3 Report

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          8 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          3 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT175_ALERT_4_G The CIF-Embedded .res File Contains SAME Records          1 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          3 Report
PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records          1 Report
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  4  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       3.63 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  4  )       1.37 Check
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         36 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          8 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.8 Low
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       55.0 Degree
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

   1 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
   7 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: X-AREA (Stoe, 2009); cell refinement: X-AREA (Stoe, 2009); data reduction: X-RED (Stoe, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

(E)-N-Phenyl-N-(phenylcarbamoyl)-3-[propyl(trimethylsilyl)amino]acrylamide chloroform hemisolvate top

Crystal data top

2C₂₂H₂₉N₃O₂Si·CHCl₃	Z = 2
M_r = 910.51	F(000) = 964
Triclinic, P1	D_x = 1.230 Mg m⁻³
a = 11.8904 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.5405 (4) Å	Cell parameters from 54315 reflections
c = 17.9387 (6) Å	θ = 1.8–27.5°
α = 107.849 (3)°	µ = 0.28 mm⁻¹
β = 95.849 (3)°	T = 153 K
γ = 101.372 (3)°	Prism, pale yellow
V = 2458.07 (15) Å³	0.45 × 0.40 × 0.15 mm

Data collection top

Stoe IPDS 2 diffractometer	11291 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	8839 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.069
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.5°, θ_min = 1.8°
rotation method scans	h = −14→15
Absorption correction: integration (X-RED; Stoe, 2009)	k = −16→16
T_min = 0.817, T_max = 0.982	l = −23→23
54315 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.055	w = 1/[σ²(F_o²) + (0.0328P)² + 2.1873P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max = 0.001
S = 1.17	Δρ_max = 0.42 e Å⁻³
11291 reflections	Δρ_min = −0.42 e Å⁻³
611 parameters	Extinction correction: SHELXL2017/1 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
36 restraints	Extinction coefficient: 0.0038 (6)
Primary atom site location: structure-invariant direct methods

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.

Refinement. Hydrogen atoms bonded to C were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å for H(phenyl), 0.99 Å for CH₂, 0.98 Å for CH₃ and 1.0 Å for H(chloroform). U_iso(H) = xU_eq(C), where x = 1.2 for H(phenyl), CH₂, and H(chloroform) and 1.5 for CH₃. Hydrogen atoms at nitrogen atoms N3A and N3B and at olefinic carbon atoms (C4A, C4B, C5A, and C5B) were localized from residual electron density maps and were freely refined.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Si1A	0.53631 (4)	0.23095 (5)	0.59880 (3)	0.01628 (12)
N1A	0.39528 (14)	0.25836 (14)	0.58740 (10)	0.0165 (3)
C1A	0.3406 (3)	0.5463 (2)	0.58109 (17)	0.0417 (6)
H1A	0.407277	0.567774	0.556240	0.063*
H1B	0.331823	0.614774	0.622488	0.063*
H1C	0.269735	0.514457	0.540719	0.063*
C2A	0.36093 (19)	0.45635 (17)	0.61797 (13)	0.0224 (4)
H2A	0.293221	0.433938	0.642521	0.027*
H2B	0.430703	0.489557	0.660316	0.027*
C3A	0.37822 (17)	0.35008 (17)	0.55549 (12)	0.0174 (4)
H3A	0.309305	0.319135	0.512453	0.021*
H3B	0.446877	0.373069	0.531950	0.021*
C4A	0.30031 (17)	0.19110 (17)	0.59944 (11)	0.0164 (4)
H4A	0.3146 (18)	0.1329 (18)	0.6216 (12)	0.011 (5)*
C5A	0.18748 (16)	0.19702 (17)	0.58591 (12)	0.0164 (4)
H5A	0.1675 (19)	0.2521 (19)	0.5644 (13)	0.017 (5)*
C6A	0.10055 (16)	0.11577 (16)	0.60454 (12)	0.0164 (4)
O1A	0.12410 (12)	0.03836 (12)	0.62846 (9)	0.0226 (3)
N2A	−0.01519 (13)	0.12775 (14)	0.59446 (10)	0.0165 (3)
C7A	−0.11611 (16)	0.04834 (16)	0.59948 (11)	0.0162 (4)
O2A	−0.21194 (12)	0.06611 (13)	0.58615 (9)	0.0228 (3)
N3A	−0.09445 (14)	−0.04211 (14)	0.61935 (11)	0.0185 (3)
H3E	−0.023 (3)	−0.042 (2)	0.6274 (17)	0.042 (8)*
C8A	−0.03738 (16)	0.23085 (17)	0.58167 (12)	0.0174 (4)
C9A	−0.09394 (17)	0.22435 (19)	0.50850 (13)	0.0222 (4)
H9A	−0.120708	0.152111	0.466889	0.027*
C10A	−0.1111 (2)	0.3249 (2)	0.49667 (15)	0.0300 (5)
H10A	−0.150059	0.321455	0.446758	0.036*
C11A	−0.0715 (2)	0.4300 (2)	0.55748 (16)	0.0314 (5)
H11A	−0.082837	0.498546	0.548986	0.038*
C12A	−0.0155 (2)	0.43556 (19)	0.63054 (15)	0.0302 (5)
H12A	0.011550	0.507836	0.672086	0.036*
C13A	0.00126 (18)	0.33547 (18)	0.64313 (13)	0.0229 (4)
H13A	0.038833	0.338711	0.693396	0.027*
C14A	−0.17583 (17)	−0.13019 (17)	0.63154 (11)	0.0171 (4)
C15A	−0.13700 (18)	−0.22580 (18)	0.63712 (13)	0.0222 (4)
H15A	−0.059669	−0.230292	0.630321	0.027*
C16A	−0.2103 (2)	−0.31462 (19)	0.65252 (14)	0.0266 (5)
H16A	−0.182804	−0.379102	0.656646	0.032*
C17A	−0.32377 (19)	−0.30915 (19)	0.66187 (14)	0.0265 (5)
H17A	−0.374055	−0.369245	0.672895	0.032*
C18A	−0.36262 (19)	−0.21519 (19)	0.65493 (13)	0.0252 (5)
H18A	−0.440576	−0.211811	0.660471	0.030*
C19A	−0.28983 (17)	−0.12550 (18)	0.64000 (12)	0.0204 (4)
H19A	−0.317862	−0.061407	0.635603	0.024*
C20A	0.64473 (18)	0.37213 (19)	0.64477 (14)	0.0264 (5)
H20A	0.645650	0.416166	0.608067	0.040*
H20B	0.722212	0.358824	0.655951	0.040*
H20C	0.623401	0.415728	0.694479	0.040*
C21A	0.5652 (2)	0.1556 (2)	0.49887 (13)	0.0276 (5)
H21A	0.500390	0.088326	0.471175	0.041*
H21B	0.637477	0.130151	0.504458	0.041*
H21C	0.572966	0.208372	0.468161	0.041*
C22A	0.53612 (18)	0.14171 (18)	0.66408 (13)	0.0223 (4)
H22A	0.512616	0.180935	0.714115	0.033*
H22B	0.614491	0.130352	0.675195	0.033*
H22C	0.481136	0.066593	0.637482	0.033*
Si1B	0.84710 (5)	0.32972 (6)	0.86670 (4)	0.02534 (15)
N1B	0.69589 (15)	0.31525 (15)	0.86978 (10)	0.0202 (4)
C1B	0.5352 (3)	0.1396 (3)	0.98522 (18)	0.0513 (8)
H1D	0.462311	0.108730	0.946681	0.077*
H1E	0.517577	0.160887	1.039283	0.077*
H1F	0.580279	0.080708	0.977980	0.077*
C2B	0.6055 (2)	0.2454 (2)	0.97240 (14)	0.0305 (5)
H2C	0.679719	0.275875	1.010775	0.037*
H2D	0.561513	0.306219	0.982118	0.037*
C3B	0.63127 (19)	0.21576 (18)	0.88774 (13)	0.0239 (4)
H3C	0.676916	0.156322	0.879165	0.029*
H3D	0.556640	0.181901	0.849921	0.029*
C4B	0.63751 (17)	0.39084 (18)	0.85520 (11)	0.0182 (4)
H4B	0.684 (2)	0.456 (2)	0.8446 (14)	0.024 (6)*
C5B	0.52209 (17)	0.38597 (18)	0.85359 (12)	0.0193 (4)
H5B	0.471 (2)	0.327 (2)	0.8650 (14)	0.022 (6)*
C6B	0.47745 (17)	0.47721 (18)	0.83768 (12)	0.0191 (4)
O1B	0.53795 (13)	0.55653 (13)	0.82116 (10)	0.0271 (3)
N2B	0.35896 (14)	0.47275 (15)	0.84306 (10)	0.0199 (4)
C7B	0.29421 (18)	0.55001 (19)	0.82724 (13)	0.0232 (4)
O2B	0.19006 (14)	0.53001 (16)	0.82805 (12)	0.0378 (4)
N3B	0.35794 (16)	0.64190 (16)	0.81410 (11)	0.0243 (4)
H3F	0.433 (2)	0.639 (2)	0.8122 (15)	0.029 (7)*
C8B	0.29571 (17)	0.38468 (18)	0.86997 (13)	0.0204 (4)
C9B	0.23157 (18)	0.28060 (19)	0.81549 (13)	0.0258 (5)
H9B	0.221522	0.269170	0.760136	0.031*
C10B	0.1821 (2)	0.1931 (2)	0.84293 (15)	0.0323 (5)
H10B	0.137461	0.121378	0.806189	0.039*
C11B	0.1977 (2)	0.2100 (2)	0.92381 (16)	0.0351 (6)
H11B	0.164941	0.149412	0.942240	0.042*
C12B	0.2608 (2)	0.3151 (2)	0.97764 (15)	0.0349 (6)
H12B	0.270886	0.326955	1.033052	0.042*
C13B	0.3092 (2)	0.4027 (2)	0.95046 (13)	0.0274 (5)
H13B	0.351729	0.475352	0.987259	0.033*
C14B	0.3177 (2)	0.7284 (2)	0.79240 (13)	0.0266 (5)
C15B	0.4012 (2)	0.8081 (2)	0.77542 (16)	0.0367 (6)
H15B	0.480185	0.803287	0.780883	0.044*
C16B	0.3704 (3)	0.8943 (3)	0.75063 (18)	0.0486 (7)
H16B	0.427997	0.947767	0.738593	0.058*
C17B	0.2558 (3)	0.9025 (3)	0.74344 (19)	0.0558 (9)
H17B	0.233786	0.960241	0.725253	0.067*
C18B	0.1740 (3)	0.8260 (3)	0.7629 (2)	0.0550 (8)
H18B	0.095737	0.833136	0.759378	0.066*
C19B	0.2029 (2)	0.7385 (2)	0.78768 (17)	0.0409 (6)
H19B	0.145420	0.686604	0.801103	0.049*
C20B	0.8620 (2)	0.2053 (2)	0.78358 (15)	0.0356 (6)
H20D	0.820354	0.133407	0.789350	0.053*
H20E	0.944585	0.205739	0.784364	0.053*
H20F	0.828826	0.210924	0.733008	0.053*
C21B	0.9185 (2)	0.3294 (3)	0.96314 (16)	0.0446 (7)
H21D	0.904945	0.393195	1.006273	0.067*
H21E	1.002374	0.338944	0.963688	0.067*
H21F	0.885862	0.256044	0.970580	0.067*
C22B	0.9033 (2)	0.4663 (2)	0.84800 (16)	0.0373 (6)
H22D	0.861469	0.463469	0.797199	0.056*
H22E	0.986645	0.476221	0.845962	0.056*
H22F	0.891493	0.531275	0.890969	0.056*
C23A	0.8351 (6)	0.8733 (6)	0.8529 (5)	0.041 (3)	0.726 (13)
H23A	0.803377	0.848695	0.794825	0.049*	0.726 (13)
Cl1A	0.8931 (3)	0.7619 (2)	0.86680 (15)	0.0594 (7)	0.726 (13)
Cl2A	0.9415 (2)	0.9989 (2)	0.8746 (3)	0.0912 (11)	0.726 (13)
Cl3A	0.7188 (3)	0.8881 (3)	0.9013 (2)	0.0756 (9)	0.726 (13)
C23B	0.8402 (11)	0.8686 (11)	0.8482 (12)	0.030 (7)	0.274 (13)
H23B	0.831173	0.856202	0.789897	0.036*	0.274 (13)
Cl1B	0.9176 (14)	0.7799 (13)	0.8780 (9)	0.138 (5)	0.274 (13)
Cl2B	0.9224 (13)	1.0053 (8)	0.9078 (10)	0.154 (5)	0.274 (13)
Cl3B	0.7109 (8)	0.8654 (13)	0.8849 (8)	0.123 (4)	0.274 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Si1A	0.0115 (2)	0.0170 (3)	0.0201 (3)	0.0027 (2)	0.0024 (2)	0.0063 (2)
N1A	0.0131 (7)	0.0162 (8)	0.0216 (8)	0.0025 (6)	0.0036 (6)	0.0087 (7)
C1A	0.0563 (17)	0.0250 (12)	0.0428 (15)	0.0159 (12)	−0.0049 (13)	0.0104 (11)
C2A	0.0225 (10)	0.0176 (10)	0.0257 (11)	0.0038 (8)	0.0019 (8)	0.0068 (8)
C3A	0.0163 (9)	0.0190 (10)	0.0195 (10)	0.0036 (7)	0.0046 (8)	0.0100 (8)
C4A	0.0161 (9)	0.0153 (9)	0.0176 (9)	0.0033 (7)	0.0026 (7)	0.0056 (8)
C5A	0.0148 (9)	0.0160 (9)	0.0195 (10)	0.0027 (7)	0.0032 (7)	0.0082 (8)
C6A	0.0132 (9)	0.0157 (9)	0.0186 (9)	0.0023 (7)	0.0016 (7)	0.0044 (7)
O1A	0.0139 (7)	0.0202 (7)	0.0379 (9)	0.0036 (6)	0.0030 (6)	0.0168 (7)
N2A	0.0113 (7)	0.0148 (8)	0.0251 (9)	0.0023 (6)	0.0032 (6)	0.0098 (7)
C7A	0.0142 (9)	0.0155 (9)	0.0179 (9)	0.0017 (7)	0.0029 (7)	0.0054 (7)
O2A	0.0130 (7)	0.0254 (8)	0.0340 (8)	0.0053 (6)	0.0045 (6)	0.0152 (7)
N3A	0.0111 (8)	0.0170 (8)	0.0291 (9)	0.0019 (6)	0.0037 (7)	0.0110 (7)
C8A	0.0130 (9)	0.0160 (9)	0.0274 (10)	0.0053 (7)	0.0081 (8)	0.0106 (8)
C9A	0.0178 (10)	0.0253 (11)	0.0274 (11)	0.0071 (8)	0.0064 (8)	0.0122 (9)
C10A	0.0296 (12)	0.0371 (13)	0.0365 (13)	0.0172 (10)	0.0105 (10)	0.0235 (11)
C11A	0.0334 (12)	0.0248 (11)	0.0511 (15)	0.0158 (10)	0.0216 (11)	0.0241 (11)
C12A	0.0302 (12)	0.0193 (11)	0.0428 (14)	0.0068 (9)	0.0150 (10)	0.0097 (10)
C13A	0.0183 (10)	0.0208 (10)	0.0305 (11)	0.0046 (8)	0.0075 (8)	0.0090 (9)
C14A	0.0164 (9)	0.0174 (9)	0.0161 (9)	0.0008 (7)	0.0028 (7)	0.0056 (8)
C15A	0.0188 (10)	0.0212 (10)	0.0278 (11)	0.0051 (8)	0.0051 (8)	0.0093 (9)
C16A	0.0290 (11)	0.0195 (10)	0.0336 (12)	0.0051 (9)	0.0072 (9)	0.0121 (9)
C17A	0.0263 (11)	0.0205 (10)	0.0309 (12)	−0.0030 (8)	0.0083 (9)	0.0102 (9)
C18A	0.0197 (10)	0.0265 (11)	0.0281 (11)	0.0008 (8)	0.0074 (9)	0.0092 (9)
C19A	0.0176 (9)	0.0193 (10)	0.0241 (10)	0.0035 (8)	0.0048 (8)	0.0073 (8)
C20A	0.0175 (10)	0.0249 (11)	0.0327 (12)	−0.0018 (8)	0.0010 (9)	0.0092 (9)
C21A	0.0248 (11)	0.0355 (13)	0.0260 (11)	0.0139 (10)	0.0080 (9)	0.0098 (10)
C22A	0.0214 (10)	0.0213 (10)	0.0243 (11)	0.0063 (8)	−0.0001 (8)	0.0083 (9)
Si1B	0.0169 (3)	0.0309 (3)	0.0231 (3)	0.0092 (2)	−0.0008 (2)	0.0010 (3)
N1B	0.0185 (8)	0.0220 (9)	0.0203 (9)	0.0074 (7)	0.0031 (7)	0.0058 (7)
C1B	0.074 (2)	0.0396 (16)	0.0452 (17)	0.0053 (15)	0.0231 (16)	0.0218 (13)
C2B	0.0401 (13)	0.0290 (12)	0.0249 (11)	0.0083 (10)	0.0080 (10)	0.0118 (10)
C3B	0.0278 (11)	0.0218 (10)	0.0241 (11)	0.0078 (9)	0.0049 (9)	0.0090 (9)
C4B	0.0189 (9)	0.0197 (10)	0.0146 (9)	0.0052 (8)	0.0024 (7)	0.0036 (8)
C5B	0.0160 (9)	0.0213 (10)	0.0206 (10)	0.0033 (8)	0.0035 (8)	0.0075 (8)
C6B	0.0148 (9)	0.0238 (10)	0.0188 (9)	0.0055 (8)	0.0042 (7)	0.0066 (8)
O1B	0.0196 (7)	0.0297 (8)	0.0401 (9)	0.0077 (6)	0.0108 (7)	0.0203 (7)
N2B	0.0152 (8)	0.0230 (9)	0.0241 (9)	0.0059 (7)	0.0060 (7)	0.0098 (7)
C7B	0.0183 (10)	0.0303 (11)	0.0230 (10)	0.0105 (8)	0.0045 (8)	0.0085 (9)
O2B	0.0182 (8)	0.0448 (10)	0.0601 (12)	0.0131 (7)	0.0119 (8)	0.0260 (9)
N3B	0.0199 (9)	0.0298 (10)	0.0305 (10)	0.0128 (8)	0.0085 (8)	0.0150 (8)
C8B	0.0142 (9)	0.0236 (10)	0.0251 (10)	0.0054 (8)	0.0067 (8)	0.0092 (8)
C9B	0.0201 (10)	0.0291 (12)	0.0243 (11)	0.0051 (9)	0.0017 (8)	0.0047 (9)
C10B	0.0238 (11)	0.0232 (11)	0.0419 (14)	−0.0014 (9)	0.0011 (10)	0.0055 (10)
C11B	0.0311 (13)	0.0322 (13)	0.0451 (15)	0.0027 (10)	0.0123 (11)	0.0186 (11)
C12B	0.0376 (13)	0.0410 (14)	0.0276 (12)	0.0034 (11)	0.0111 (10)	0.0157 (11)
C13B	0.0299 (12)	0.0269 (11)	0.0223 (11)	0.0020 (9)	0.0073 (9)	0.0060 (9)
C14B	0.0331 (12)	0.0293 (12)	0.0206 (10)	0.0166 (10)	0.0038 (9)	0.0072 (9)
C15B	0.0431 (14)	0.0407 (14)	0.0422 (14)	0.0221 (12)	0.0183 (12)	0.0252 (12)
C16B	0.071 (2)	0.0455 (16)	0.0507 (17)	0.0310 (15)	0.0246 (15)	0.0307 (14)
C17B	0.080 (2)	0.0543 (19)	0.0565 (19)	0.0459 (18)	0.0158 (17)	0.0323 (16)
C18B	0.0489 (18)	0.0583 (19)	0.069 (2)	0.0346 (16)	0.0026 (16)	0.0257 (17)
C19B	0.0315 (13)	0.0446 (15)	0.0537 (17)	0.0200 (12)	0.0046 (12)	0.0204 (13)
C20B	0.0276 (12)	0.0426 (14)	0.0321 (13)	0.0156 (11)	0.0061 (10)	0.0014 (11)
C21B	0.0331 (14)	0.0607 (18)	0.0323 (14)	0.0209 (13)	−0.0098 (11)	0.0036 (13)
C22B	0.0191 (11)	0.0428 (15)	0.0422 (15)	0.0002 (10)	0.0059 (10)	0.0075 (12)
C23A	0.050 (5)	0.043 (5)	0.038 (4)	0.007 (4)	0.008 (4)	0.028 (4)
Cl1A	0.0840 (13)	0.0599 (11)	0.0711 (12)	0.0407 (9)	0.0421 (9)	0.0503 (8)
Cl2A	0.0638 (11)	0.0482 (10)	0.156 (3)	−0.0127 (8)	0.0034 (13)	0.0478 (13)
Cl3A	0.0710 (16)	0.1108 (16)	0.0802 (18)	0.0586 (14)	0.0431 (13)	0.0494 (13)
C23B	0.010 (7)	0.019 (9)	0.046 (12)	−0.001 (6)	0.006 (7)	−0.010 (7)
Cl1B	0.115 (7)	0.169 (9)	0.192 (10)	0.101 (7)	0.059 (6)	0.097 (7)
Cl2B	0.160 (8)	0.101 (5)	0.133 (8)	−0.081 (5)	−0.054 (6)	0.039 (5)
Cl3B	0.046 (3)	0.248 (10)	0.062 (4)	0.002 (4)	0.015 (2)	0.056 (5)

Geometric parameters (Å, º) top

Si1A—N1A	1.7811 (17)	N1B—C4B	1.350 (3)
Si1A—C22A	1.851 (2)	N1B—C3B	1.473 (3)
Si1A—C21A	1.855 (2)	C1B—C2B	1.518 (3)
Si1A—C20A	1.861 (2)	C1B—H1D	0.9800
N1A—C4A	1.349 (2)	C1B—H1E	0.9800
N1A—C3A	1.471 (2)	C1B—H1F	0.9800
C1A—C2A	1.517 (3)	C2B—C3B	1.527 (3)
C1A—H1A	0.9800	C2B—H2C	0.9900
C1A—H1B	0.9800	C2B—H2D	0.9900
C1A—H1C	0.9800	C3B—H3C	0.9900
C2A—C3A	1.521 (3)	C3B—H3D	0.9900
C2A—H2A	0.9900	C4B—C5B	1.359 (3)
C2A—H2B	0.9900	C4B—H4B	0.97 (2)
C3A—H3A	0.9900	C5B—C6B	1.443 (3)
C3A—H3B	0.9900	C5B—H5B	0.95 (2)
C4A—C5A	1.360 (3)	C6B—O1B	1.240 (2)
C4A—H4A	0.97 (2)	C6B—N2B	1.413 (2)
C5A—C6A	1.443 (3)	N2B—C7B	1.425 (3)
C5A—H5A	0.94 (2)	N2B—C8B	1.446 (3)
C6A—O1A	1.242 (2)	C7B—O2B	1.217 (3)
C6A—N2A	1.413 (2)	C7B—N3B	1.348 (3)
N2A—C7A	1.430 (2)	N3B—C14B	1.409 (3)
N2A—C8A	1.448 (2)	N3B—H3F	0.90 (3)
C7A—O2A	1.218 (2)	C8B—C13B	1.378 (3)
C7A—N3A	1.351 (2)	C8B—C9B	1.383 (3)
N3A—C14A	1.405 (2)	C9B—C10B	1.388 (3)
N3A—H3E	0.85 (3)	C9B—H9B	0.9500
C8A—C9A	1.384 (3)	C10B—C11B	1.388 (4)
C8A—C13A	1.386 (3)	C10B—H10B	0.9500
C9A—C10A	1.390 (3)	C11B—C12B	1.383 (4)
C9A—H9A	0.9500	C11B—H11B	0.9500
C10A—C11A	1.385 (4)	C12B—C13B	1.383 (3)
C10A—H10A	0.9500	C12B—H12B	0.9500
C11A—C12A	1.383 (4)	C13B—H13B	0.9500
C11A—H11A	0.9500	C14B—C15B	1.390 (3)
C12A—C13A	1.389 (3)	C14B—C19B	1.391 (3)
C12A—H12A	0.9500	C15B—C16B	1.385 (3)
C13A—H13A	0.9500	C15B—H15B	0.9500
C14A—C19A	1.390 (3)	C16B—C17B	1.382 (4)
C14A—C15A	1.394 (3)	C16B—H16B	0.9500
C15A—C16A	1.390 (3)	C17B—C18B	1.377 (5)
C15A—H15A	0.9500	C17B—H17B	0.9500
C16A—C17A	1.389 (3)	C18B—C19B	1.391 (4)
C16A—H16A	0.9500	C18B—H18B	0.9500
C17A—C18A	1.382 (3)	C19B—H19B	0.9500
C17A—H17A	0.9500	C20B—H20D	0.9800
C18A—C19A	1.391 (3)	C20B—H20E	0.9800
C18A—H18A	0.9500	C20B—H20F	0.9800
C19A—H19A	0.9500	C21B—H21D	0.9800
C20A—H20A	0.9800	C21B—H21E	0.9800
C20A—H20B	0.9800	C21B—H21F	0.9800
C20A—H20C	0.9800	C22B—H22D	0.9800
C21A—H21A	0.9800	C22B—H22E	0.9800
C21A—H21B	0.9800	C22B—H22F	0.9800
C21A—H21C	0.9800	C23A—Cl3A	1.717 (7)
C22A—H22A	0.9800	C23A—Cl2A	1.724 (6)
C22A—H22B	0.9800	C23A—Cl1A	1.745 (6)
C22A—H22C	0.9800	C23A—H23A	1.0000
Si1B—N1B	1.7794 (18)	C23B—Cl3B	1.731 (13)
Si1B—C21B	1.849 (3)	C23B—Cl2B	1.743 (13)
Si1B—C20B	1.851 (2)	C23B—Cl1B	1.744 (13)
Si1B—C22B	1.854 (3)	C23B—H23B	1.0000

N1A—Si1A—C22A	107.35 (9)	C4B—N1B—C3B	118.60 (17)
N1A—Si1A—C21A	108.35 (9)	C4B—N1B—Si1B	122.71 (15)
C22A—Si1A—C21A	111.95 (10)	C3B—N1B—Si1B	118.69 (14)
N1A—Si1A—C20A	108.14 (9)	C2B—C1B—H1D	109.5
C22A—Si1A—C20A	111.09 (10)	C2B—C1B—H1E	109.5
C21A—Si1A—C20A	109.82 (11)	H1D—C1B—H1E	109.5
C4A—N1A—C3A	117.89 (16)	C2B—C1B—H1F	109.5
C4A—N1A—Si1A	122.62 (13)	H1D—C1B—H1F	109.5
C3A—N1A—Si1A	119.17 (12)	H1E—C1B—H1F	109.5
C2A—C1A—H1A	109.5	C1B—C2B—C3B	110.7 (2)
C2A—C1A—H1B	109.5	C1B—C2B—H2C	109.5
H1A—C1A—H1B	109.5	C3B—C2B—H2C	109.5
C2A—C1A—H1C	109.5	C1B—C2B—H2D	109.5
H1A—C1A—H1C	109.5	C3B—C2B—H2D	109.5
H1B—C1A—H1C	109.5	H2C—C2B—H2D	108.1
C1A—C2A—C3A	110.74 (19)	N1B—C3B—C2B	113.99 (18)
C1A—C2A—H2A	109.5	N1B—C3B—H3C	108.8
C3A—C2A—H2A	109.5	C2B—C3B—H3C	108.8
C1A—C2A—H2B	109.5	N1B—C3B—H3D	108.8
C3A—C2A—H2B	109.5	C2B—C3B—H3D	108.8
H2A—C2A—H2B	108.1	H3C—C3B—H3D	107.6
N1A—C3A—C2A	113.24 (16)	N1B—C4B—C5B	127.4 (2)
N1A—C3A—H3A	108.9	N1B—C4B—H4B	115.3 (14)
C2A—C3A—H3A	108.9	C5B—C4B—H4B	117.3 (14)
N1A—C3A—H3B	108.9	C4B—C5B—C6B	118.43 (19)
C2A—C3A—H3B	108.9	C4B—C5B—H5B	122.5 (14)
H3A—C3A—H3B	107.7	C6B—C5B—H5B	119.0 (14)
N1A—C4A—C5A	127.93 (18)	O1B—C6B—N2B	120.82 (18)
N1A—C4A—H4A	115.9 (13)	O1B—C6B—C5B	123.17 (18)
C5A—C4A—H4A	116.2 (13)	N2B—C6B—C5B	116.00 (17)
C4A—C5A—C6A	117.71 (18)	C6B—N2B—C7B	126.47 (17)
C4A—C5A—H5A	120.5 (14)	C6B—N2B—C8B	118.35 (16)
C6A—C5A—H5A	121.8 (14)	C7B—N2B—C8B	115.13 (16)
O1A—C6A—N2A	120.42 (17)	O2B—C7B—N3B	126.1 (2)
O1A—C6A—C5A	122.79 (17)	O2B—C7B—N2B	119.1 (2)
N2A—C6A—C5A	116.79 (17)	N3B—C7B—N2B	114.74 (18)
C6A—N2A—C7A	125.79 (16)	C7B—N3B—C14B	127.68 (19)
C6A—N2A—C8A	119.34 (15)	C7B—N3B—H3F	113.3 (16)
C7A—N2A—C8A	114.80 (15)	C14B—N3B—H3F	118.3 (16)
O2A—C7A—N3A	125.61 (18)	C13B—C8B—C9B	120.9 (2)
O2A—C7A—N2A	119.39 (17)	C13B—C8B—N2B	118.55 (19)
N3A—C7A—N2A	114.99 (16)	C9B—C8B—N2B	120.27 (19)
C7A—N3A—C14A	127.20 (17)	C8B—C9B—C10B	119.0 (2)
C7A—N3A—H3E	114.3 (19)	C8B—C9B—H9B	120.5
C14A—N3A—H3E	118.4 (19)	C10B—C9B—H9B	120.5
C9A—C8A—C13A	121.06 (19)	C11B—C10B—C9B	120.3 (2)
C9A—C8A—N2A	120.05 (18)	C11B—C10B—H10B	119.9
C13A—C8A—N2A	118.87 (18)	C9B—C10B—H10B	119.9
C8A—C9A—C10A	119.1 (2)	C12B—C11B—C10B	120.1 (2)
C8A—C9A—H9A	120.4	C12B—C11B—H11B	120.0
C10A—C9A—H9A	120.4	C10B—C11B—H11B	120.0
C11A—C10A—C9A	120.2 (2)	C11B—C12B—C13B	119.7 (2)
C11A—C10A—H10A	119.9	C11B—C12B—H12B	120.1
C9A—C10A—H10A	119.9	C13B—C12B—H12B	120.1
C12A—C11A—C10A	120.3 (2)	C8B—C13B—C12B	120.0 (2)
C12A—C11A—H11A	119.9	C8B—C13B—H13B	120.0
C10A—C11A—H11A	119.9	C12B—C13B—H13B	120.0
C11A—C12A—C13A	120.0 (2)	C15B—C14B—C19B	119.6 (2)
C11A—C12A—H12A	120.0	C15B—C14B—N3B	115.8 (2)
C13A—C12A—H12A	120.0	C19B—C14B—N3B	124.6 (2)
C8A—C13A—C12A	119.4 (2)	C16B—C15B—C14B	120.7 (3)
C8A—C13A—H13A	120.3	C16B—C15B—H15B	119.7
C12A—C13A—H13A	120.3	C14B—C15B—H15B	119.7
C19A—C14A—C15A	119.24 (18)	C17B—C16B—C15B	119.9 (3)
C19A—C14A—N3A	123.88 (18)	C17B—C16B—H16B	120.1
C15A—C14A—N3A	116.86 (17)	C15B—C16B—H16B	120.1
C16A—C15A—C14A	120.64 (19)	C18B—C17B—C16B	119.3 (3)
C16A—C15A—H15A	119.7	C18B—C17B—H17B	120.4
C14A—C15A—H15A	119.7	C16B—C17B—H17B	120.4
C17A—C16A—C15A	120.0 (2)	C17B—C18B—C19B	121.7 (3)
C17A—C16A—H16A	120.0	C17B—C18B—H18B	119.1
C15A—C16A—H16A	120.0	C19B—C18B—H18B	119.1
C18A—C17A—C16A	119.18 (19)	C18B—C19B—C14B	118.7 (3)
C18A—C17A—H17A	120.4	C18B—C19B—H19B	120.7
C16A—C17A—H17A	120.4	C14B—C19B—H19B	120.7
C17A—C18A—C19A	121.3 (2)	Si1B—C20B—H20D	109.5
C17A—C18A—H18A	119.4	Si1B—C20B—H20E	109.5
C19A—C18A—H18A	119.4	H20D—C20B—H20E	109.5
C14A—C19A—C18A	119.61 (19)	Si1B—C20B—H20F	109.5
C14A—C19A—H19A	120.2	H20D—C20B—H20F	109.5
C18A—C19A—H19A	120.2	H20E—C20B—H20F	109.5
Si1A—C20A—H20A	109.5	Si1B—C21B—H21D	109.5
Si1A—C20A—H20B	109.5	Si1B—C21B—H21E	109.5
H20A—C20A—H20B	109.5	H21D—C21B—H21E	109.5
Si1A—C20A—H20C	109.5	Si1B—C21B—H21F	109.5
H20A—C20A—H20C	109.5	H21D—C21B—H21F	109.5
H20B—C20A—H20C	109.5	H21E—C21B—H21F	109.5
Si1A—C21A—H21A	109.5	Si1B—C22B—H22D	109.5
Si1A—C21A—H21B	109.5	Si1B—C22B—H22E	109.5
H21A—C21A—H21B	109.5	H22D—C22B—H22E	109.5
Si1A—C21A—H21C	109.5	Si1B—C22B—H22F	109.5
H21A—C21A—H21C	109.5	H22D—C22B—H22F	109.5
H21B—C21A—H21C	109.5	H22E—C22B—H22F	109.5
Si1A—C22A—H22A	109.5	Cl3A—C23A—Cl2A	114.7 (4)
Si1A—C22A—H22B	109.5	Cl3A—C23A—Cl1A	111.0 (3)
H22A—C22A—H22B	109.5	Cl2A—C23A—Cl1A	111.6 (4)
Si1A—C22A—H22C	109.5	Cl3A—C23A—H23A	106.3
H22A—C22A—H22C	109.5	Cl2A—C23A—H23A	106.3
H22B—C22A—H22C	109.5	Cl1A—C23A—H23A	106.3
N1B—Si1B—C21B	107.54 (11)	Cl3B—C23B—Cl2B	100.9 (10)
N1B—Si1B—C20B	107.58 (10)	Cl3B—C23B—Cl1B	111.2 (11)
C21B—Si1B—C20B	111.25 (13)	Cl2B—C23B—Cl1B	101.4 (10)
N1B—Si1B—C22B	107.87 (10)	Cl3B—C23B—H23B	113.9
C21B—Si1B—C22B	112.33 (13)	Cl2B—C23B—H23B	113.9
C20B—Si1B—C22B	110.07 (13)	Cl1B—C23B—H23B	113.9

C22A—Si1A—N1A—C4A	−21.84 (18)	C21B—Si1B—N1B—C4B	125.21 (18)
C21A—Si1A—N1A—C4A	99.24 (17)	C20B—Si1B—N1B—C4B	−114.87 (18)
C20A—Si1A—N1A—C4A	−141.78 (16)	C22B—Si1B—N1B—C4B	3.8 (2)
C22A—Si1A—N1A—C3A	164.85 (14)	C21B—Si1B—N1B—C3B	−55.77 (19)
C21A—Si1A—N1A—C3A	−74.06 (17)	C20B—Si1B—N1B—C3B	64.16 (18)
C20A—Si1A—N1A—C3A	44.92 (17)	C22B—Si1B—N1B—C3B	−177.14 (16)
C4A—N1A—C3A—C2A	78.7 (2)	C4B—N1B—C3B—C2B	−77.2 (2)
Si1A—N1A—C3A—C2A	−107.67 (17)	Si1B—N1B—C3B—C2B	103.69 (19)
C1A—C2A—C3A—N1A	−178.50 (18)	C1B—C2B—C3B—N1B	178.0 (2)
C3A—N1A—C4A—C5A	−0.2 (3)	C3B—N1B—C4B—C5B	−1.2 (3)
Si1A—N1A—C4A—C5A	−173.63 (17)	Si1B—N1B—C4B—C5B	177.81 (17)
N1A—C4A—C5A—C6A	−179.24 (19)	N1B—C4B—C5B—C6B	179.22 (19)
C4A—C5A—C6A—O1A	−3.5 (3)	C4B—C5B—C6B—O1B	4.0 (3)
C4A—C5A—C6A—N2A	176.38 (18)	C4B—C5B—C6B—N2B	−175.07 (18)
O1A—C6A—N2A—C7A	−8.7 (3)	O1B—C6B—N2B—C7B	3.4 (3)
C5A—C6A—N2A—C7A	171.41 (18)	C5B—C6B—N2B—C7B	−177.51 (19)
O1A—C6A—N2A—C8A	168.05 (18)	O1B—C6B—N2B—C8B	−174.14 (19)
C5A—C6A—N2A—C8A	−11.9 (3)	C5B—C6B—N2B—C8B	5.0 (3)
C6A—N2A—C7A—O2A	−176.81 (19)	C6B—N2B—C7B—O2B	174.0 (2)
C8A—N2A—C7A—O2A	6.3 (3)	C8B—N2B—C7B—O2B	−8.4 (3)
C6A—N2A—C7A—N3A	3.2 (3)	C6B—N2B—C7B—N3B	−7.3 (3)
C8A—N2A—C7A—N3A	−173.61 (17)	C8B—N2B—C7B—N3B	170.29 (18)
O2A—C7A—N3A—C14A	−2.6 (3)	O2B—C7B—N3B—C14B	−5.6 (4)
N2A—C7A—N3A—C14A	177.31 (18)	N2B—C7B—N3B—C14B	175.8 (2)
C6A—N2A—C8A—C9A	111.0 (2)	C6B—N2B—C8B—C13B	80.3 (2)
C7A—N2A—C8A—C9A	−72.0 (2)	C7B—N2B—C8B—C13B	−97.5 (2)
C6A—N2A—C8A—C13A	−67.6 (2)	C6B—N2B—C8B—C9B	−94.0 (2)
C7A—N2A—C8A—C13A	109.5 (2)	C7B—N2B—C8B—C9B	88.2 (2)
C13A—C8A—C9A—C10A	0.6 (3)	C13B—C8B—C9B—C10B	−1.1 (3)
N2A—C8A—C9A—C10A	−177.96 (18)	N2B—C8B—C9B—C10B	173.11 (19)
C8A—C9A—C10A—C11A	0.2 (3)	C8B—C9B—C10B—C11B	−0.4 (3)
C9A—C10A—C11A—C12A	−0.5 (3)	C9B—C10B—C11B—C12B	1.2 (4)
C10A—C11A—C12A—C13A	0.0 (3)	C10B—C11B—C12B—C13B	−0.6 (4)
C9A—C8A—C13A—C12A	−1.1 (3)	C9B—C8B—C13B—C12B	1.7 (3)
N2A—C8A—C13A—C12A	177.48 (18)	N2B—C8B—C13B—C12B	−172.6 (2)
C11A—C12A—C13A—C8A	0.8 (3)	C11B—C12B—C13B—C8B	−0.9 (4)
C7A—N3A—C14A—C19A	−13.1 (3)	C7B—N3B—C14B—C15B	−174.3 (2)
C7A—N3A—C14A—C15A	168.4 (2)	C7B—N3B—C14B—C19B	6.1 (4)
C19A—C14A—C15A—C16A	−1.3 (3)	C19B—C14B—C15B—C16B	−2.7 (4)
N3A—C14A—C15A—C16A	177.3 (2)	N3B—C14B—C15B—C16B	177.6 (2)
C14A—C15A—C16A—C17A	0.5 (3)	C14B—C15B—C16B—C17B	0.7 (4)
C15A—C16A—C17A—C18A	0.6 (3)	C15B—C16B—C17B—C18B	1.5 (5)
C16A—C17A—C18A—C19A	−1.0 (3)	C16B—C17B—C18B—C19B	−1.8 (5)
C15A—C14A—C19A—C18A	0.9 (3)	C17B—C18B—C19B—C14B	−0.2 (5)
N3A—C14A—C19A—C18A	−177.53 (19)	C15B—C14B—C19B—C18B	2.5 (4)
C17A—C18A—C19A—C14A	0.2 (3)	N3B—C14B—C19B—C18B	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg1is the centroid of the C14A–C19A phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3E···O1A	0.85 (3)	1.83 (3)	2.564 (2)	144 (3)
N3B—H3F···O1B	0.90 (3)	1.80 (3)	2.584 (2)	144 (2)
C19A—H19A···O2A	0.95	2.29	2.880 (2)	120
C19B—H19B···O2B	0.95	2.30	2.900 (3)	120
C9A—H9A···O1Aⁱ	0.95	2.46	3.378 (3)	161
C23A—H23A···Cg1ⁱⁱ	1.00	2.51	3.498 (8)	172
C23B—H23B···Cg1ⁱⁱ	1.00	2.47	3.43 (2)	161

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

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(E)-N-Phenyl-N-(phenyl­carbamo­yl)-3-[prop­yl(tri­methyl­sil­yl)amino]­acryl­amide chloro­form hemisolvate

Supporting information

Key indicators

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(E)-N-Phenyl-N-(phenylcarbamoyl)-3-[propyl(trimethylsilyl)amino]acrylamide chloroform hemisolvate