The synthesis, crystal structure and Hirshfeld analysis of 4-(3,4-di­methyl­anilino)-N-(3,4-di­methyl­phen­yl)quinoline-3-carboxamide

The quinoline moiety of the title quinoline carboxamide derivative is not planar as a result of a slight puckering of the pyridine ring. The secondary amine has a slightly pyramidal geometry.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.094
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.200
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT414_ALERT_2_C Short Intra D-H..H-X       H2       ..H32              1.93 Ang.
                                                      x,y,z  =      1_555 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.239 Check

Alert level G
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT916_ALERT_2_G Hooft y and Flack x Parameter Values Differ by .       0.32 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: OSCAIL (McArdle et al., 2004) and SHELXT (Sheldrick, 2015a); program(s) used to refine structure: OSCAIL (McArdle et al., 2004), ShelXle (Hübschle et al., 2011) and SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: OSCAIL (McArdle et al., 2004), SHELXL2014 (Sheldrick, 2015b) and PLATON (Spek, 2020).

4-(3,4-Dimethylanilino)-N-(3,4-dimethylphenyl)quinoline-3-carboxamide

Crystal data

C26H25N3O	Dx = 1.283 Mg m^−3
Mr = 395.49	Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, P212121	Cell parameters from 5133 reflections
a = 6.2502 (3) Å	θ = 1.6–27.0°
b = 15.7915 (6) Å	µ = 0.08 mm^−1
c = 20.7395 (9) Å	T = 100 K
V = 2046.99 (15) Å^3	Needle, yellow
Z = 4	0.30 × 0.05 × 0.01 mm
F(000) = 840

Data collection

Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector diffractometer	3754 independent reflections
Radiation source: Rotating Anode, Rigaku FRE+	3390 reflections with I > 2σ(I)
Confocal mirrors, VHF Varimax monochromator	Rint = 0.089
Detector resolution: 10 pixels mm^-1	θmax = 25.4°, θmin = 1.6°
profile data from ω–scans	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2018)	k = −19→19
Tmin = 0.487, Tmax = 1.000	l = −24→24
28997 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.5091P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3754 reflections	Δρmax = 0.22 e Å^−3
287 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Absolute structure: Flack x determined using 1238 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (10)

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.

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

	x	y	z	Uiso*/Ueq
O31	0.5597 (3)	0.49964 (12)	0.49759 (10)	0.0221 (5)
N1	−0.0092 (4)	0.69133 (14)	0.44267 (11)	0.0174 (5)
N32	0.5344 (4)	0.62696 (15)	0.54659 (11)	0.0162 (5)
H32	0.470 (5)	0.678 (2)	0.5477 (15)	0.028 (9)*
N41	0.2497 (4)	0.44714 (15)	0.42129 (13)	0.0195 (5)
H41	0.368 (6)	0.441 (2)	0.4400 (16)	0.026 (9)*
C2	0.1722 (5)	0.66921 (17)	0.47005 (13)	0.0161 (6)
H2	0.233 (5)	0.7147 (17)	0.4948 (14)	0.014 (7)*
C3	0.2727 (4)	0.58912 (17)	0.46478 (13)	0.0154 (6)
C4	0.1727 (5)	0.52774 (16)	0.42608 (13)	0.0158 (6)
C5	−0.1008 (5)	0.50493 (18)	0.33862 (13)	0.0196 (6)
H5	−0.037379	0.452194	0.327658	0.024*
C4A	−0.0119 (4)	0.55400 (17)	0.38887 (13)	0.0161 (6)
C6	−0.2769 (5)	0.53228 (19)	0.30555 (15)	0.0237 (7)
H6	−0.332691	0.499128	0.271220	0.028*
C7	−0.3757 (5)	0.60896 (19)	0.32201 (15)	0.0241 (7)
H7	−0.504081	0.625506	0.300995	0.029*
C8	−0.2880 (5)	0.65997 (19)	0.36813 (14)	0.0209 (6)
H8	−0.352964	0.712802	0.377996	0.025*
C8A	−0.1007 (5)	0.63448 (17)	0.40134 (13)	0.0160 (6)
C31	0.4680 (4)	0.56876 (16)	0.50328 (13)	0.0158 (6)
C321	0.7023 (4)	0.61744 (16)	0.59179 (13)	0.0146 (6)
C322	0.6840 (5)	0.66241 (17)	0.64919 (14)	0.0173 (6)
H322	0.559581	0.695626	0.656408	0.021*
C323	0.8416 (4)	0.66032 (18)	0.69622 (14)	0.0184 (6)
C324	1.0277 (5)	0.61192 (18)	0.68531 (13)	0.0181 (6)
C325	1.0432 (5)	0.56727 (18)	0.62795 (14)	0.0191 (6)
H325	1.167921	0.534397	0.620254	0.023*
C326	0.8845 (4)	0.56865 (17)	0.58145 (14)	0.0168 (6)
H326	0.899709	0.536669	0.542929	0.020*
C327	0.8115 (5)	0.70814 (19)	0.75834 (15)	0.0250 (7)
H32A	0.934273	0.745612	0.765419	0.037*
H32B	0.800307	0.667948	0.794181	0.037*
H32C	0.680368	0.741992	0.755852	0.037*
C328	1.2038 (5)	0.6077 (2)	0.73465 (15)	0.0254 (7)
H32D	1.253251	0.665128	0.744633	0.038*
H32E	1.323221	0.574413	0.717458	0.038*
H32F	1.149786	0.580841	0.774012	0.038*
C411	0.1222 (5)	0.37148 (17)	0.41833 (14)	0.0194 (6)
C412	0.2064 (5)	0.30036 (17)	0.38929 (13)	0.0202 (7)
H412	0.346385	0.302560	0.371508	0.024*
C413	0.0886 (5)	0.22452 (18)	0.38552 (13)	0.0192 (6)
C414	−0.1149 (5)	0.22182 (18)	0.41275 (14)	0.0208 (7)
C415	−0.1955 (5)	0.29255 (18)	0.44308 (14)	0.0228 (7)
H415	−0.333552	0.290071	0.462158	0.027*
C416	−0.0793 (5)	0.36751 (18)	0.44637 (14)	0.0200 (6)
H416	−0.137324	0.415606	0.467629	0.024*
C417	0.1826 (5)	0.14893 (18)	0.35187 (16)	0.0275 (7)
H41D	0.090414	0.132683	0.315709	0.041*
H41E	0.193326	0.101625	0.382290	0.041*
H41F	0.325447	0.163163	0.335672	0.041*
C418	−0.2461 (5)	0.14148 (19)	0.40803 (16)	0.0281 (7)
H41A	−0.384750	0.150125	0.429087	0.042*
H41B	−0.169739	0.095098	0.429390	0.042*
H41C	−0.268722	0.127195	0.362554	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O31	0.0180 (10)	0.0128 (9)	0.0356 (12)	0.0031 (8)	−0.0017 (9)	−0.0058 (9)
N1	0.0155 (12)	0.0137 (11)	0.0229 (13)	−0.0001 (10)	0.0022 (11)	−0.0008 (10)
N32	0.0136 (12)	0.0114 (11)	0.0236 (13)	0.0014 (10)	−0.0003 (10)	−0.0012 (10)
N41	0.0152 (13)	0.0120 (12)	0.0314 (14)	0.0002 (10)	−0.0025 (12)	−0.0058 (10)
C2	0.0173 (14)	0.0107 (13)	0.0202 (15)	−0.0031 (12)	0.0028 (12)	−0.0018 (11)
C3	0.0133 (14)	0.0137 (13)	0.0194 (14)	−0.0012 (12)	0.0052 (12)	−0.0011 (11)
C4	0.0152 (14)	0.0139 (13)	0.0184 (15)	−0.0010 (11)	0.0042 (12)	−0.0010 (11)
C5	0.0203 (15)	0.0159 (14)	0.0226 (15)	−0.0033 (13)	0.0013 (13)	−0.0032 (12)
C4A	0.0146 (14)	0.0146 (14)	0.0193 (14)	−0.0032 (12)	0.0040 (12)	0.0013 (11)
C6	0.0273 (17)	0.0212 (15)	0.0224 (15)	−0.0067 (14)	−0.0068 (14)	−0.0013 (12)
C7	0.0203 (16)	0.0232 (16)	0.0287 (17)	−0.0014 (13)	−0.0065 (13)	0.0028 (13)
C8	0.0195 (15)	0.0171 (14)	0.0260 (16)	0.0008 (13)	0.0010 (13)	0.0024 (12)
C8A	0.0164 (14)	0.0138 (13)	0.0179 (14)	−0.0031 (12)	0.0048 (12)	−0.0003 (11)
C31	0.0145 (14)	0.0123 (12)	0.0208 (15)	−0.0020 (12)	0.0057 (12)	0.0000 (12)
C321	0.0136 (14)	0.0103 (13)	0.0200 (14)	−0.0020 (11)	0.0009 (12)	0.0035 (11)
C322	0.0163 (14)	0.0118 (13)	0.0238 (16)	−0.0002 (12)	0.0036 (12)	0.0004 (11)
C323	0.0171 (14)	0.0180 (14)	0.0202 (15)	−0.0030 (13)	0.0036 (12)	0.0041 (11)
C324	0.0159 (15)	0.0152 (14)	0.0232 (15)	−0.0035 (12)	0.0031 (12)	0.0057 (12)
C325	0.0138 (14)	0.0168 (14)	0.0267 (16)	0.0018 (12)	0.0048 (12)	0.0032 (12)
C326	0.0151 (14)	0.0148 (13)	0.0205 (15)	−0.0018 (11)	0.0034 (12)	−0.0011 (12)
C327	0.0246 (16)	0.0234 (16)	0.0269 (17)	0.0001 (14)	0.0022 (14)	−0.0033 (13)
C328	0.0186 (16)	0.0316 (17)	0.0261 (16)	−0.0015 (14)	0.0003 (13)	0.0025 (13)
C411	0.0241 (16)	0.0132 (13)	0.0208 (15)	−0.0013 (12)	−0.0066 (13)	−0.0002 (12)
C412	0.0225 (16)	0.0174 (14)	0.0209 (16)	0.0005 (13)	−0.0013 (13)	0.0001 (12)
C413	0.0279 (17)	0.0128 (14)	0.0171 (15)	0.0022 (12)	−0.0057 (13)	−0.0007 (11)
C414	0.0223 (16)	0.0205 (15)	0.0197 (16)	−0.0021 (12)	−0.0065 (13)	0.0028 (12)
C415	0.0198 (15)	0.0252 (16)	0.0235 (16)	−0.0019 (13)	−0.0022 (13)	0.0035 (12)
C416	0.0206 (15)	0.0150 (14)	0.0245 (16)	0.0005 (12)	−0.0025 (13)	−0.0018 (12)
C417	0.0307 (17)	0.0171 (15)	0.0347 (18)	−0.0001 (14)	0.0016 (15)	−0.0046 (13)
C418	0.0298 (18)	0.0213 (16)	0.0333 (18)	−0.0062 (14)	−0.0042 (15)	0.0036 (13)

Geometric parameters (Å, º)

O31—C31	1.238 (3)	C323—C327	1.505 (4)
N1—C2	1.315 (4)	C324—C325	1.386 (4)
N1—C8A	1.367 (4)	C324—C328	1.505 (4)
N32—C31	1.350 (3)	C325—C326	1.384 (4)
N32—C321	1.416 (4)	C325—H325	0.9500
N32—H32	0.90 (4)	C326—H326	0.9500
N41—C4	1.364 (3)	C327—H32A	0.9800
N41—C411	1.437 (4)	C327—H32B	0.9800
N41—H41	0.84 (4)	C327—H32C	0.9800
C2—C3	1.416 (4)	C328—H32D	0.9800
C2—H2	0.96 (3)	C328—H32E	0.9800
C3—C4	1.405 (4)	C328—H32F	0.9800
C3—C31	1.494 (4)	C411—C412	1.379 (4)
C4—C4A	1.449 (4)	C411—C416	1.389 (4)
C5—C6	1.367 (4)	C412—C413	1.408 (4)
C5—C4A	1.413 (4)	C412—H412	0.9500
C5—H5	0.9500	C413—C414	1.392 (4)
C4A—C8A	1.411 (4)	C413—C417	1.503 (4)
C6—C7	1.401 (4)	C414—C415	1.377 (4)
C6—H6	0.9500	C414—C418	1.514 (4)
C7—C8	1.365 (4)	C415—C416	1.390 (4)
C7—H7	0.9500	C415—H415	0.9500
C8—C8A	1.417 (4)	C416—H416	0.9500
C8—H8	0.9500	C417—H41D	0.9800
C321—C322	1.391 (4)	C417—H41E	0.9800
C321—C326	1.391 (4)	C417—H41F	0.9800
C322—C323	1.387 (4)	C418—H41A	0.9800
C322—H322	0.9500	C418—H41B	0.9800
C323—C324	1.410 (4)	C418—H41C	0.9800
C2—N1—C8A	117.2 (2)	C326—C325—C324	122.7 (3)
C31—N32—C321	126.6 (2)	C326—C325—H325	118.7
C31—N32—H32	119 (2)	C324—C325—H325	118.7
C321—N32—H32	114 (2)	C325—C326—C321	119.2 (3)
C4—N41—C411	125.7 (2)	C325—C326—H326	120.4
C4—N41—H41	112 (2)	C321—C326—H326	120.4
C411—N41—H41	115 (2)	C323—C327—H32A	109.5
N1—C2—C3	125.9 (3)	C323—C327—H32B	109.5
N1—C2—H2	111.9 (17)	H32A—C327—H32B	109.5
C3—C2—H2	122.2 (17)	C323—C327—H32C	109.5
C4—C3—C2	117.6 (3)	H32A—C327—H32C	109.5
C4—C3—C31	121.3 (2)	H32B—C327—H32C	109.5
C2—C3—C31	120.9 (2)	C324—C328—H32D	109.5
N41—C4—C3	121.9 (3)	C324—C328—H32E	109.5
N41—C4—C4A	120.6 (2)	H32D—C328—H32E	109.5
C3—C4—C4A	117.4 (2)	C324—C328—H32F	109.5
C6—C5—C4A	120.9 (3)	H32D—C328—H32F	109.5
C6—C5—H5	119.5	H32E—C328—H32F	109.5
C4A—C5—H5	119.5	C412—C411—C416	119.5 (3)
C8A—C4A—C5	118.3 (3)	C412—C411—N41	119.0 (3)
C8A—C4A—C4	118.3 (2)	C416—C411—N41	121.5 (2)
C5—C4A—C4	123.3 (3)	C411—C412—C413	121.2 (3)
C5—C6—C7	120.4 (3)	C411—C412—H412	119.4
C5—C6—H6	119.8	C413—C412—H412	119.4
C7—C6—H6	119.8	C414—C413—C412	118.8 (3)
C8—C7—C6	120.3 (3)	C414—C413—C417	121.4 (3)
C8—C7—H7	119.9	C412—C413—C417	119.8 (3)
C6—C7—H7	119.9	C415—C414—C413	119.6 (3)
C7—C8—C8A	120.3 (3)	C415—C414—C418	120.7 (3)
C7—C8—H8	119.9	C413—C414—C418	119.6 (3)
C8A—C8—H8	119.9	C414—C415—C416	121.5 (3)
N1—C8A—C4A	122.8 (3)	C414—C415—H415	119.3
N1—C8A—C8	117.7 (3)	C416—C415—H415	119.3
C4A—C8A—C8	119.5 (3)	C411—C416—C415	119.4 (3)
O31—C31—N32	121.4 (3)	C411—C416—H416	120.3
O31—C31—C3	121.1 (2)	C415—C416—H416	120.3
N32—C31—C3	117.4 (2)	C413—C417—H41D	109.5
C322—C321—C326	118.8 (3)	C413—C417—H41E	109.5
C322—C321—N32	116.8 (2)	H41D—C417—H41E	109.5
C326—C321—N32	124.3 (2)	C413—C417—H41F	109.5
C323—C322—C321	122.1 (3)	H41D—C417—H41F	109.5
C323—C322—H322	119.0	H41E—C417—H41F	109.5
C321—C322—H322	119.0	C414—C418—H41A	109.5
C322—C323—C324	119.1 (3)	C414—C418—H41B	109.5
C322—C323—C327	120.1 (3)	H41A—C418—H41B	109.5
C324—C323—C327	120.8 (3)	C414—C418—H41C	109.5
C325—C324—C323	118.1 (3)	H41A—C418—H41C	109.5
C325—C324—C328	120.7 (3)	H41B—C418—H41C	109.5
C323—C324—C328	121.2 (3)
C8A—N1—C2—C3	−5.5 (4)	C2—C3—C31—N32	5.0 (4)
N1—C2—C3—C4	1.1 (4)	C31—N32—C321—C322	−150.3 (3)
N1—C2—C3—C31	−174.0 (3)	C31—N32—C321—C326	31.7 (4)
C411—N41—C4—C3	141.0 (3)	C326—C321—C322—C323	0.2 (4)
C411—N41—C4—C4A	−41.6 (4)	N32—C321—C322—C323	−177.9 (2)
C2—C3—C4—N41	−175.7 (3)	C321—C322—C323—C324	0.8 (4)
C31—C3—C4—N41	−0.6 (4)	C321—C322—C323—C327	−178.3 (3)
C2—C3—C4—C4A	6.8 (4)	C322—C323—C324—C325	−0.9 (4)
C31—C3—C4—C4A	−178.1 (2)	C327—C323—C324—C325	178.1 (3)
C6—C5—C4A—C8A	−4.1 (4)	C322—C323—C324—C328	179.8 (3)
C6—C5—C4A—C4	179.2 (3)	C327—C323—C324—C328	−1.2 (4)
N41—C4—C4A—C8A	172.4 (3)	C323—C324—C325—C326	0.1 (4)
C3—C4—C4A—C8A	−10.1 (4)	C328—C324—C325—C326	179.4 (3)
N41—C4—C4A—C5	−10.8 (4)	C324—C325—C326—C321	0.8 (4)
C3—C4—C4A—C5	166.7 (3)	C322—C321—C326—C325	−1.0 (4)
C4A—C5—C6—C7	−1.5 (4)	N32—C321—C326—C325	176.9 (2)
C5—C6—C7—C8	4.7 (5)	C4—N41—C411—C412	155.0 (3)
C6—C7—C8—C8A	−2.2 (4)	C4—N41—C411—C416	−27.8 (4)
C2—N1—C8A—C4A	1.7 (4)	C416—C411—C412—C413	2.3 (4)
C2—N1—C8A—C8	−175.7 (2)	N41—C411—C412—C413	179.6 (3)
C5—C4A—C8A—N1	−170.9 (3)	C411—C412—C413—C414	−1.1 (4)
C4—C4A—C8A—N1	6.0 (4)	C411—C412—C413—C417	178.3 (3)
C5—C4A—C8A—C8	6.4 (4)	C412—C413—C414—C415	−0.5 (4)
C4—C4A—C8A—C8	−176.7 (2)	C417—C413—C414—C415	−179.9 (3)
C7—C8—C8A—N1	174.1 (3)	C412—C413—C414—C418	178.7 (3)
C7—C8—C8A—C4A	−3.4 (4)	C417—C413—C414—C418	−0.6 (4)
C321—N32—C31—O31	−3.1 (4)	C413—C414—C415—C416	1.0 (4)
C321—N32—C31—C3	173.8 (2)	C418—C414—C415—C416	−178.3 (3)
C4—C3—C31—O31	6.9 (4)	C412—C411—C416—C415	−1.8 (4)
C2—C3—C31—O31	−178.1 (3)	N41—C411—C416—C415	−179.1 (3)
C4—C3—C31—N32	−170.0 (3)	C414—C415—C416—C411	0.2 (4)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the N1/C2–C4/C4A/C8A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N41—H41···O31	0.84 (4)	1.93 (3)	2.635 (3)	142 (3)
C326—H326···O31	0.95	2.40	2.887 (3)	112
N32—H32···N1^i	0.90 (4)	2.07 (4)	2.891 (3)	150 (3)
C2—H2···N1^i	0.96 (3)	2.55 (3)	3.477 (4)	163 (2)
C416—H416···O31^ii	0.95	2.39	3.252 (4)	150
C326—H326···Cg^iii	0.95	2.82	3.398 (3)	120

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