4-Chloro-1,1-di­phenyl-3-(1-pyrrolyl)-2-aza­buta-1,3-diene

The title compound, C₁₉H₁₅ClN₂, is the sole stable product resulting from nucleophilic attack of the sodium salt of pyrrole on 4,4-di­chloro-1,1-di­phenyl-2-aza­buta-1,3-diene. The mech­an­ism of its formation is briefly discussed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: PROCESS in MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

4-chloro-1,1-diphenyl-3-(1-pyrrolyl)-2-azabuta-1,3-diene

Crystal data

C19H15ClN2	Z = 4
Mr = 306.78	F(000) = 640
Triclinic, P1	Dx = 1.258 Mg m^−3
Hall symbol: -P 1	Melting point: 372.5 K
a = 9.910 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.411 (1) Å	Cell parameters from 25 reflections
c = 16.401 (1) Å	θ = 4.8–18.6°
α = 89.88 (1)°	µ = 0.23 mm^−1
β = 73.19 (1)°	T = 293 K
γ = 88.89 (1)°	Prism, yellow
V = 1619.5 (2) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.013
Radiation source: fine-focus sealed tube	θmax = 26.3°, θmin = 2.2°
Graphite monochromator	h = −12→0
ω scans	k = −12→12
6954 measured reflections	l = −20→19
6557 independent reflections	3 standard reflections every 120 min
4267 reflections with I > 2σ(I)	intensity decay: −1.2%

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 0.3756P] where P = (Fo^2 + 2Fc^2)/3
6557 reflections	(Δ/σ)max < 0.001
397 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.35 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.

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

	x	y	z	Uiso*/Ueq
Cl1	0.13324 (7)	0.86982 (6)	0.48071 (4)	0.0769 (2)
Cl2	0.56180 (7)	0.98774 (8)	0.82113 (5)	0.1012 (2)
N1	0.2201 (2)	0.58748 (15)	0.47916 (9)	0.0511 (4)
N2	0.3418 (2)	0.5851 (2)	0.33288 (9)	0.0543 (4)
N3	0.2668 (2)	1.1086 (2)	0.85370 (10)	0.0584 (4)
N4	0.2847 (2)	1.2357 (2)	0.96760 (11)	0.0582 (4)
C1	0.2286 (2)	0.7791 (2)	0.39555 (13)	0.0619 (5)
H1	0.2542	0.8158	0.34162	0.080*
C2	0.2666 (2)	0.6586 (2)	0.40436 (11)	0.0502 (4)
C3	0.2625 (2)	0.6109 (2)	0.54447 (11)	0.0451 (4)
C4	0.3437 (2)	0.4539 (2)	0.32744 (14)	0.0638 (5)
H4	0.3035	0.3975	0.37141	0.083*
C5	0.4153 (3)	0.4211 (3)	0.2458 (2)	0.0773 (7)
H5	0.4329	0.3380	0.2242	0.100*
C6	0.4572 (3)	0.5331 (3)	0.20063 (15)	0.0800 (7)
H6	0.5075	0.5385	0.14331	0.104*
C7	0.4126 (2)	0.6324 (3)	0.25422 (13)	0.0702 (6)
H7	0.4271	0.7188	0.24045	0.091*
C8	0.1913 (2)	0.5425 (2)	0.62453 (11)	0.0456 (4)
C9	0.2586 (2)	0.5218 (2)	0.68703 (12)	0.0545 (5)
H9	0.3482	0.5538	0.67993	0.071*
C10	0.1931 (2)	0.4540 (2)	0.75957 (13)	0.0660 (6)
H10	0.2393	0.4390	0.80070	0.086*
C11	0.0602 (2)	0.4086 (2)	0.77113 (14)	0.0714 (6)
H11	0.0159	0.3634	0.82026	0.093*
C12	−0.0078 (2)	0.4298 (2)	0.71002 (14)	0.0738 (6)
H12	−0.0984	0.3995	0.71824	0.096*
C13	0.0570 (2)	0.4956 (2)	0.63700 (13)	0.0618 (5)
H13	0.0106	0.5086	0.59574	0.080*
C14	0.3803 (2)	0.6980 (2)	0.54401 (11)	0.0476 (4)
C15	0.5090 (2)	0.6823 (2)	0.48275 (13)	0.0610 (5)
H15	0.5212	0.6181	0.44180	0.079*
C16	0.6190 (3)	0.7614 (3)	0.4821 (2)	0.0841 (7)
H16	0.7057	0.7495	0.4413	0.109*
C17	0.6011 (3)	0.8575 (3)	0.5415 (2)	0.0958 (9)
H17	0.6753	0.9114	0.5405	0.124*
C18	0.4732 (3)	0.8744 (2)	0.6026 (2)	0.0868 (8)
H18	0.4611	0.9400	0.6426	0.113*
C19	0.3631 (2)	0.7943 (2)	0.60467 (14)	0.0644 (5)
H19	0.2774	0.8048	0.64664	0.084*
C20	0.4797 (2)	1.0992 (2)	0.8971 (2)	0.0735 (6)
H20	0.5289	1.1316	0.9327	0.096*
C21	0.3495 (2)	1.1406 (2)	0.90685 (13)	0.0587 (5)
C22	0.2086 (2)	0.9988 (2)	0.85826 (11)	0.0480 (4)
C23	0.3338 (3)	1.2844 (2)	1.0318 (2)	0.0789 (7)
H23	0.4183	1.2611	1.0422	0.103*
C24	0.2390 (3)	1.3708 (2)	1.0765 (2)	0.0816 (7)
H24	0.2466	1.4178	1.1231	0.106*
C25	0.1271 (3)	1.3775 (2)	1.0408 (2)	0.0732 (6)
H25	0.0469	1.4299	1.0591	0.095*
C26	0.1566 (2)	1.2943 (2)	0.97498 (14)	0.0639 (6)
H26	0.0994	1.2791	0.94015	0.083*
C27	0.2146 (2)	0.9003 (2)	0.92355 (11)	0.0466 (4)
C28	0.1716 (2)	0.9324 (2)	1.00925 (11)	0.0494 (4)
H28	0.1366	1.0147	1.02611	0.064*
C29	0.1806 (2)	0.8429 (2)	1.06968 (13)	0.0570 (5)
H29	0.1515	0.8650	1.12713	0.074*
C30	0.2324 (2)	0.7217 (2)	1.04531 (14)	0.0631 (6)
H30	0.2395	0.6618	1.08614	0.082*
C31	0.2736 (2)	0.6884 (2)	0.9608 (2)	0.0671 (6)
H31	0.3080	0.6057	0.9446	0.087*
C32	0.2646 (2)	0.7766 (2)	0.89968 (13)	0.0588 (5)
H32	0.2921	0.7531	0.84247	0.076*
C33	0.1259 (2)	0.9739 (2)	0.79766 (11)	0.0484 (4)
C34	0.1333 (2)	1.0586 (2)	0.73066 (12)	0.0582 (5)
H34	0.1944	1.1273	0.72220	0.076*
C35	0.0513 (2)	1.0415 (2)	0.67704 (13)	0.0689 (6)
H35	0.0573	1.0986	0.63251	0.090*
C36	−0.0395 (2)	0.9404 (2)	0.68882 (14)	0.0722 (6)
H36	−0.0954	0.9296	0.65262	0.094*
C37	−0.0476 (2)	0.8555 (2)	0.75399 (14)	0.0699 (6)
H37	−0.1083	0.7867	0.76162	0.091*
C38	0.0346 (2)	0.8721 (2)	0.80855 (12)	0.0579 (5)
H38	0.0283	0.8144	0.85281	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0956 (5)	0.0733 (4)	0.0657 (3)	0.0217 (3)	−0.0311 (3)	−0.0108 (3)
Cl2	0.0704 (4)	0.1091 (5)	0.1151 (6)	0.0043 (4)	−0.0130 (4)	0.0015 (4)
N1	0.0535 (9)	0.0602 (9)	0.0411 (8)	−0.0051 (7)	−0.0158 (7)	0.0011 (7)
N2	0.0538 (9)	0.0682 (11)	0.0426 (8)	−0.0001 (8)	−0.0167 (7)	−0.0017 (7)
N3	0.0687 (11)	0.0570 (10)	0.0562 (10)	−0.0094 (8)	−0.0282 (9)	0.0081 (8)
N4	0.0659 (11)	0.0569 (10)	0.0622 (10)	−0.0156 (8)	−0.0342 (9)	0.0095 (8)
C1	0.0722 (14)	0.0693 (14)	0.0477 (11)	0.0034 (11)	−0.0230 (10)	0.0030 (10)
C2	0.0497 (11)	0.0622 (12)	0.0418 (10)	−0.0042 (9)	−0.0179 (8)	−0.0007 (8)
C3	0.0420 (10)	0.0498 (10)	0.0434 (9)	0.0024 (8)	−0.0122 (8)	−0.0013 (8)
C4	0.0649 (13)	0.0677 (14)	0.0634 (13)	0.0052 (11)	−0.0264 (11)	−0.0063 (10)
C5	0.071 (2)	0.093 (2)	0.074 (2)	0.0201 (13)	−0.0313 (13)	−0.0297 (14)
C6	0.0664 (15)	0.119 (2)	0.0520 (13)	0.0108 (14)	−0.0137 (11)	−0.0122 (14)
C7	0.0662 (14)	0.092 (2)	0.0484 (12)	−0.0012 (12)	−0.0106 (10)	0.0035 (11)
C8	0.0414 (10)	0.0528 (10)	0.0418 (9)	−0.0011 (8)	−0.0107 (8)	−0.0010 (8)
C9	0.0439 (10)	0.0719 (13)	0.0481 (10)	−0.0065 (9)	−0.0137 (9)	0.0075 (9)
C10	0.0568 (13)	0.092 (2)	0.0527 (12)	−0.0090 (11)	−0.0210 (10)	0.0174 (11)
C11	0.0625 (14)	0.094 (2)	0.0562 (12)	−0.0191 (12)	−0.0146 (11)	0.0232 (12)
C12	0.0520 (13)	0.104 (2)	0.0673 (14)	−0.0274 (12)	−0.0181 (11)	0.0189 (13)
C13	0.0489 (11)	0.0854 (15)	0.0545 (12)	−0.0105 (10)	−0.0197 (10)	0.0095 (10)
C14	0.0470 (10)	0.0517 (10)	0.0471 (10)	−0.0027 (8)	−0.0181 (8)	0.0069 (8)
C15	0.0521 (12)	0.0728 (13)	0.0579 (12)	−0.0054 (10)	−0.0155 (10)	0.0083 (10)
C16	0.0571 (14)	0.103 (2)	0.091 (2)	−0.0245 (14)	−0.0182 (13)	0.024 (2)
C17	0.085 (2)	0.089 (2)	0.126 (2)	−0.042 (2)	−0.048 (2)	0.026 (2)
C18	0.100 (2)	0.069 (2)	0.105 (2)	−0.0185 (15)	−0.050 (2)	−0.0055 (14)
C19	0.0680 (14)	0.0626 (13)	0.0667 (13)	−0.0050 (11)	−0.0258 (11)	−0.0043 (10)
C20	0.0612 (14)	0.082 (2)	0.081 (2)	−0.0132 (12)	−0.0258 (12)	0.0096 (13)
C21	0.0619 (13)	0.0601 (12)	0.0611 (12)	−0.0193 (10)	−0.0276 (10)	0.0194 (10)
C22	0.0475 (10)	0.0523 (11)	0.0424 (10)	0.0019 (8)	−0.0103 (8)	0.0010 (8)
C23	0.088 (2)	0.080 (2)	0.089 (2)	−0.0149 (14)	−0.0577 (15)	0.0042 (14)
C24	0.114 (2)	0.0665 (15)	0.081 (2)	−0.0121 (15)	−0.054 (2)	−0.0035 (13)
C25	0.092 (2)	0.0581 (13)	0.078 (2)	−0.0078 (12)	−0.0368 (14)	0.0047 (11)
C26	0.0727 (14)	0.0610 (12)	0.0702 (14)	−0.0132 (11)	−0.0395 (12)	0.0105 (11)
C27	0.0411 (10)	0.0502 (10)	0.0483 (10)	−0.0036 (8)	−0.0125 (8)	0.0027 (8)
C28	0.0466 (10)	0.0531 (11)	0.0480 (10)	−0.0040 (8)	−0.0127 (8)	0.0015 (8)
C29	0.0518 (11)	0.0696 (13)	0.0502 (11)	−0.0093 (10)	−0.0151 (9)	0.0088 (10)
C30	0.0519 (12)	0.0665 (14)	0.0714 (14)	−0.0054 (10)	−0.0185 (11)	0.0236 (11)
C31	0.0602 (13)	0.0528 (12)	0.083 (2)	0.0068 (10)	−0.0126 (11)	0.0069 (11)
C32	0.0588 (12)	0.0573 (12)	0.0554 (12)	0.0041 (10)	−0.0092 (10)	−0.0028 (9)
C33	0.0498 (11)	0.0532 (11)	0.0410 (9)	0.0038 (8)	−0.0117 (8)	−0.0058 (8)
C34	0.0659 (13)	0.0617 (12)	0.0493 (11)	0.0007 (10)	−0.0206 (10)	0.0009 (9)
C35	0.0762 (15)	0.082 (2)	0.0534 (12)	0.0016 (13)	−0.0275 (11)	0.0062 (11)
C36	0.0698 (15)	0.099 (2)	0.0543 (12)	0.0021 (13)	−0.0285 (11)	−0.0077 (12)
C37	0.0657 (14)	0.084 (2)	0.0631 (13)	−0.0128 (12)	−0.0226 (11)	−0.0061 (12)
C38	0.0613 (12)	0.0652 (12)	0.0477 (11)	−0.0058 (10)	−0.0163 (10)	−0.0002 (9)

Geometric parameters (Å, º)

Cl1—C1	1.715 (2)	C16—H16	0.93
Cl2—C20	1.716 (3)	C17—C18	1.379 (4)
N1—C3	1.284 (2)	C17—H17	0.93
N1—C2	1.396 (2)	C18—C19	1.379 (3)
N2—C4	1.368 (3)	C18—H18	0.93
N2—C7	1.374 (3)	C19—H19	0.93
N2—C2	1.412 (2)	C20—C21	1.317 (3)
N3—C22	1.283 (2)	C20—H20	0.93
N3—C21	1.402 (2)	C22—C33	1.486 (3)
N4—C26	1.371 (3)	C22—C27	1.494 (2)
N4—C23	1.382 (3)	C23—C24	1.342 (4)
N4—C21	1.412 (3)	C23—H23	0.93
C1—C2	1.323 (3)	C24—C25	1.397 (3)
C1—H1	0.93	C24—H24	0.93
C3—C8	1.486 (2)	C25—C26	1.346 (3)
C3—C14	1.491 (2)	C25—H25	0.93
C4—C5	1.362 (3)	C26—H26	0.93
C4—H4	0.93	C27—C28	1.385 (2)
C5—C6	1.385 (4)	C27—C32	1.386 (3)
C5—H5	0.93	C28—C29	1.379 (3)
C6—C7	1.341 (3)	C28—H28	0.93
C6—H6	0.93	C29—C30	1.369 (3)
C7—H7	0.93	C29—H29	0.93
C8—C13	1.386 (3)	C30—C31	1.369 (3)
C8—C9	1.389 (2)	C30—H30	0.93
C9—C10	1.379 (3)	C31—C32	1.379 (3)
C9—H9	0.93	C31—H31	0.93
C10—C11	1.368 (3)	C32—H32	0.93
C10—H10	0.93	C33—C38	1.384 (3)
C11—C12	1.376 (3)	C33—C34	1.394 (3)
C11—H11	0.93	C34—C35	1.373 (3)
C12—C13	1.373 (3)	C34—H34	0.93
C12—H12	0.93	C35—C36	1.375 (3)
C13—H13	0.93	C35—H35	0.93
C14—C15	1.383 (3)	C36—C37	1.371 (3)
C14—C19	1.386 (3)	C36—H36	0.93
C15—C16	1.377 (3)	C37—C38	1.386 (3)
C15—H15	0.93	C37—H37	0.93
C16—C17	1.370 (4)	C38—H38	0.93
C3—N1—C2	121.5 (2)	C19—C18—H18	119.9
C4—N2—C7	108.1 (2)	C18—C19—C14	119.8 (2)
C4—N2—C2	125.5 (2)	C18—C19—H19	120.1
C7—N2—C2	126.0 (2)	C14—C19—H19	120.08
C22—N3—C21	121.5 (2)	C21—C20—Cl2	122.4 (2)
C26—N4—C23	107.0 (2)	C21—C20—H20	118.78
C26—N4—C21	125.4 (2)	Cl2—C20—H20	118.78
C23—N4—C21	127.6 (2)	C20—C21—N3	125.1 (2)
C2—C1—Cl1	121.9 (2)	C20—C21—N4	121.9 (2)
C2—C1—H1	119.04	N3—C21—N4	112.6 (2)
Cl1—C1—H1	119.04	N3—C22—C33	117.1 (2)
C1—C2—N1	124.7 (2)	N3—C22—C27	123.2 (2)
C1—C2—N2	120.8 (2)	C33—C22—C27	119.7 (2)
N1—C2—N2	113.9 (2)	C24—C23—N4	108.6 (2)
N1—C3—C8	117.1 (2)	C24—C23—H23	125.70
N1—C3—C14	124.3 (2)	N4—C23—H23	125.70
C8—C3—C14	118.58 (15)	C23—C24—C25	107.9 (2)
C5—C4—N2	107.5 (2)	C23—C24—H24	126.06
C5—C4—H4	126.3	C25—C24—H24	126.1
N2—C4—H4	126.27	C26—C25—C24	107.5 (2)
C4—C5—C6	108.1 (2)	C26—C25—H25	126.27
C4—C5—H5	126.0	C24—C25—H25	126.3
C6—C5—H5	125.96	C25—C26—N4	109.0 (2)
C7—C6—C5	107.9 (2)	C25—C26—H26	125.50
C7—C6—H6	126.1	N4—C26—H26	125.50
C5—C6—H6	126.06	C28—C27—C32	119.1 (2)
C6—C7—N2	108.4 (2)	C28—C27—C22	120.0 (2)
C6—C7—H7	125.8	C32—C27—C22	120.9 (2)
N2—C7—H7	125.78	C29—C28—C27	120.3 (2)
C13—C8—C9	118.8 (2)	C29—C28—H28	119.85
C13—C8—C3	120.1 (2)	C27—C28—H28	119.85
C9—C8—C3	121.1 (2)	C30—C29—C28	120.2 (2)
C10—C9—C8	120.3 (2)	C30—C29—H29	119.92
C10—C9—H9	119.83	C28—C29—H29	119.92
C8—C9—H9	119.83	C29—C30—C31	120.0 (2)
C11—C10—C9	120.1 (2)	C29—C30—H30	119.99
C11—C10—H10	119.93	C31—C30—H30	119.99
C9—C10—H10	119.93	C30—C31—C32	120.5 (2)
C10—C11—C12	119.9 (2)	C30—C31—H31	119.75
C10—C11—H11	120.03	C32—C31—H31	119.75
C12—C11—H11	120.03	C31—C32—C27	119.9 (2)
C13—C12—C11	120.5 (2)	C31—C32—H32	120.03
C13—C12—H12	119.76	C27—C32—H32	120.03
C11—C12—H12	119.76	C38—C33—C34	118.5 (2)
C12—C13—C8	120.3 (2)	C38—C33—C22	121.7 (2)
C12—C13—H13	119.87	C34—C33—C22	119.7 (2)
C8—C13—H13	119.87	C35—C34—C33	120.6 (2)
C15—C14—C19	119.4 (2)	C35—C34—H34	119.71
C15—C14—C3	119.7 (2)	C33—C34—H34	119.71
C19—C14—C3	120.8 (2)	C34—C35—C36	120.4 (2)
C16—C15—C14	120.3 (2)	C34—C35—H35	119.82
C16—C15—H15	119.9	C36—C35—H35	119.82
C14—C15—H15	119.86	C37—C36—C35	119.9 (2)
C17—C16—C15	120.1 (2)	C37—C36—H36	120.05
C17—C16—H16	119.9	C35—C36—H36	120.05
C15—C16—H16	119.9	C36—C37—C38	120.2 (2)
C16—C17—C18	120.1 (2)	C36—C37—H37	119.92
C16—C17—H17	120.0	C38—C37—H37	119.92
C18—C17—H17	120.0	C33—C38—C37	120.5 (2)
C17—C18—C19	120.2 (2)	C33—C38—H38	119.75
C17—C18—H18	119.9	C37—C38—H38	119.75