5,5′-(1-Phenyl­ethane-1,1-di­yl)bis­(1H-pyrrole-2-carboxaldehyde)

In the title compound, C₁₈H₁₆N₂O₂, the dihedral angle between the pyrrole rings is 79.47 (9)°, with the N—H groups approximately orthogonal (H—N...N—H pseudo torsion angle = −106°). In the crystal, N—H...O hydrogen bonds link the mol­ecules into [11] chains. A C—H...O inter­action is also observed.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.050
• wR factor = 0.142
• Data-to-parameter ratio = 21.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.534 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        604 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

5,5'-(1-Phenylethane-1,1-diyl)bis(1H-pyrrole-2-carboxaldehyde)

Crystal data

C18H16N2O2	Z = 2
Mr = 292.33	F(000) = 308
Triclinic, P1	Dx = 1.292 Mg m^−3
a = 7.0679 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.6856 (4) Å	Cell parameters from 5094 reflections
c = 12.1510 (5) Å	θ = 3.7–29.9°
α = 101.560 (3)°	µ = 0.09 mm^−1
β = 93.302 (3)°	T = 293 K
γ = 111.270 (4)°	Cube, colourless
V = 751.66 (5) Å^3	0.18 × 0.15 × 0.13 mm

Data collection

XtaLAB Pro: Kappa dual offset/far diffractometer	Rint = 0.022
Radiation source: fine-focus sealed X-ray tube	θmax = 31.1°, θmin = 3.1°
ω scans	h = −9→10
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −13→13
Tmin = 0.901, Tmax = 1.000	l = −17→17
13274 measured reflections	Standard reflections: see text; every none reflections
4208 independent reflections	intensity decay: none
3307 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.050	H-atom parameters constrained
wR(F^2) = 0.142	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 0.1364P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4208 reflections	Δρmax = 0.32 e Å^−3
200 parameters	Δρmin = −0.19 e Å^−3
0 restraints

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
N1	0.69498 (16)	0.13760 (11)	0.87005 (8)	0.0348 (2)
H1	0.592279	0.131280	0.906260	0.042*
N2	0.94852 (16)	0.52913 (11)	0.69220 (8)	0.0350 (2)
H2	0.897693	0.470214	0.625766	0.042*
O2	1.18939 (19)	0.67425 (13)	0.53044 (9)	0.0593 (3)
O1	0.63340 (19)	−0.10500 (15)	0.98826 (12)	0.0649 (3)
C8	0.87280 (19)	0.50458 (13)	0.78942 (10)	0.0349 (3)
C13	0.53349 (18)	0.30398 (14)	0.68621 (10)	0.0346 (3)
C6	0.8011 (2)	0.04229 (15)	0.86453 (11)	0.0399 (3)
C3	0.77809 (19)	0.24329 (14)	0.80925 (10)	0.0347 (3)
C2	0.69195 (19)	0.36169 (13)	0.79432 (10)	0.0338 (2)
C11	1.1197 (2)	0.66317 (14)	0.71604 (11)	0.0398 (3)
C14	0.4611 (2)	0.40434 (16)	0.64815 (12)	0.0445 (3)
H14	0.512212	0.506479	0.686836	0.053*
C18	0.4538 (2)	0.15255 (16)	0.62642 (12)	0.0452 (3)
H18	0.500715	0.083660	0.650140	0.054*
C7	0.7592 (2)	−0.07648 (17)	0.92390 (13)	0.0471 (3)
H7	0.835458	−0.137403	0.912050	0.057*
C12	1.2317 (2)	0.72554 (15)	0.63178 (13)	0.0464 (3)
H12	1.348509	0.814225	0.657358	0.056*
C9	0.9961 (2)	0.62497 (16)	0.87798 (11)	0.0470 (3)
H9	0.978635	0.637712	0.954118	0.056*
C5	0.9541 (2)	0.09002 (19)	0.79891 (13)	0.0505 (3)
H5	1.049116	0.046264	0.780729	0.061*
C1	0.5846 (3)	0.40046 (18)	0.89673 (12)	0.0478 (3)
H1A	0.677390	0.429200	0.965753	0.072*
H1B	0.465129	0.312760	0.898067	0.072*
H1C	0.544689	0.483480	0.889915	0.072*
C10	1.1508 (2)	0.72322 (16)	0.83195 (12)	0.0500 (3)
H10	1.255985	0.812989	0.871959	0.060*
C4	0.9407 (2)	0.21604 (18)	0.76469 (13)	0.0495 (3)
H4	1.025661	0.271584	0.720018	0.059*
C15	0.3139 (2)	0.3539 (2)	0.55333 (14)	0.0543 (4)
H15	0.267142	0.422408	0.528760	0.065*
C17	0.3053 (2)	0.10196 (19)	0.53181 (15)	0.0574 (4)
H17	0.252517	−0.000256	0.493242	0.069*
C16	0.2361 (2)	0.2028 (2)	0.49507 (15)	0.0587 (4)
H16	0.137392	0.169268	0.431307	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0370 (5)	0.0360 (5)	0.0340 (5)	0.0132 (4)	0.0090 (4)	0.0142 (4)
N2	0.0403 (5)	0.0302 (5)	0.0283 (5)	0.0065 (4)	0.0053 (4)	0.0066 (4)
O2	0.0674 (7)	0.0533 (6)	0.0445 (6)	0.0066 (5)	0.0180 (5)	0.0121 (5)
O1	0.0602 (7)	0.0681 (7)	0.0862 (9)	0.0277 (6)	0.0297 (6)	0.0500 (7)
C8	0.0428 (6)	0.0322 (5)	0.0298 (5)	0.0134 (5)	0.0067 (4)	0.0090 (4)
C13	0.0334 (5)	0.0372 (6)	0.0361 (6)	0.0122 (5)	0.0132 (4)	0.0154 (5)
C6	0.0428 (6)	0.0395 (6)	0.0410 (6)	0.0172 (5)	0.0057 (5)	0.0147 (5)
C3	0.0404 (6)	0.0355 (6)	0.0300 (5)	0.0135 (5)	0.0095 (4)	0.0126 (4)
C2	0.0419 (6)	0.0336 (5)	0.0304 (5)	0.0157 (5)	0.0130 (4)	0.0129 (4)
C11	0.0420 (6)	0.0316 (6)	0.0398 (6)	0.0069 (5)	0.0042 (5)	0.0090 (5)
C14	0.0451 (7)	0.0405 (7)	0.0518 (8)	0.0176 (6)	0.0084 (6)	0.0168 (6)
C18	0.0481 (7)	0.0379 (6)	0.0485 (7)	0.0141 (6)	0.0066 (6)	0.0124 (5)
C7	0.0457 (7)	0.0445 (7)	0.0589 (8)	0.0201 (6)	0.0090 (6)	0.0237 (6)
C12	0.0457 (7)	0.0344 (6)	0.0493 (8)	0.0031 (5)	0.0105 (6)	0.0106 (5)
C9	0.0616 (8)	0.0420 (7)	0.0301 (6)	0.0133 (6)	0.0037 (6)	0.0057 (5)
C5	0.0530 (8)	0.0583 (9)	0.0560 (8)	0.0320 (7)	0.0202 (6)	0.0246 (7)
C1	0.0636 (9)	0.0518 (8)	0.0415 (7)	0.0306 (7)	0.0270 (6)	0.0191 (6)
C10	0.0560 (8)	0.0386 (7)	0.0404 (7)	0.0050 (6)	−0.0015 (6)	0.0036 (5)
C4	0.0522 (8)	0.0569 (8)	0.0554 (8)	0.0276 (7)	0.0270 (6)	0.0303 (7)
C15	0.0474 (8)	0.0620 (9)	0.0625 (9)	0.0251 (7)	0.0064 (7)	0.0270 (8)
C17	0.0521 (8)	0.0481 (8)	0.0589 (9)	0.0100 (7)	0.0009 (7)	0.0036 (7)
C16	0.0433 (8)	0.0718 (11)	0.0548 (9)	0.0165 (7)	−0.0016 (6)	0.0143 (8)

Geometric parameters (Å, º)

N1—C3	1.3622 (14)	C14—C15	1.384 (2)
N1—C6	1.3793 (16)	C14—H14	0.9300
N1—H1	0.8600	C18—C17	1.388 (2)
N2—C8	1.3533 (15)	C18—H18	0.9300
N2—C11	1.3795 (16)	C7—H7	0.9300
N2—H2	0.8600	C12—H12	0.9300
O2—C12	1.2071 (18)	C9—C10	1.394 (2)
O1—C7	1.2113 (18)	C9—H9	0.9300
C8—C9	1.3888 (18)	C5—C4	1.398 (2)
C8—C2	1.5202 (16)	C5—H5	0.9300
C13—C18	1.3867 (19)	C1—H1A	0.9600
C13—C14	1.3907 (18)	C1—H1B	0.9600
C13—C2	1.5410 (17)	C1—H1C	0.9600
C6—C5	1.3798 (19)	C10—H10	0.9300
C6—C7	1.4288 (18)	C4—H4	0.9300
C3—C4	1.3850 (18)	C15—C16	1.380 (3)
C3—C2	1.5152 (17)	C15—H15	0.9300
C2—C1	1.5470 (16)	C17—C16	1.374 (3)
C11—C10	1.3833 (19)	C17—H17	0.9300
C11—C12	1.4261 (18)	C16—H16	0.9300
C3—N1—C6	109.44 (10)	O1—C7—C6	125.90 (14)
C3—N1—H1	125.3	O1—C7—H7	117.0
C6—N1—H1	125.3	C6—C7—H7	117.0
C8—N2—C11	109.55 (10)	O2—C12—C11	126.24 (13)
C8—N2—H2	125.2	O2—C12—H12	116.9
C11—N2—H2	125.2	C11—C12—H12	116.9
N2—C8—C9	107.91 (11)	C8—C9—C10	107.53 (12)
N2—C8—C2	123.11 (10)	C8—C9—H9	126.2
C9—C8—C2	128.86 (11)	C10—C9—H9	126.2
C18—C13—C14	118.02 (12)	C6—C5—C4	107.65 (12)
C18—C13—C2	122.18 (11)	C6—C5—H5	126.2
C14—C13—C2	119.76 (11)	C4—C5—H5	126.2
N1—C6—C5	107.49 (11)	C2—C1—H1A	109.5
N1—C6—C7	123.62 (12)	C2—C1—H1B	109.5
C5—C6—C7	128.80 (13)	H1A—C1—H1B	109.5
N1—C3—C4	107.70 (11)	C2—C1—H1C	109.5
N1—C3—C2	122.84 (10)	H1A—C1—H1C	109.5
C4—C3—C2	129.42 (11)	H1B—C1—H1C	109.5
C3—C2—C8	106.88 (10)	C11—C10—C9	107.68 (12)
C3—C2—C13	111.23 (10)	C11—C10—H10	126.2
C8—C2—C13	111.41 (9)	C9—C10—H10	126.2
C3—C2—C1	110.70 (9)	C3—C4—C5	107.72 (12)
C8—C2—C1	108.65 (10)	C3—C4—H4	126.1
C13—C2—C1	107.96 (11)	C5—C4—H4	126.1
N2—C11—C10	107.32 (11)	C16—C15—C14	120.39 (15)
N2—C11—C12	123.89 (12)	C16—C15—H15	119.8
C10—C11—C12	128.73 (13)	C14—C15—H15	119.8
C15—C14—C13	120.75 (14)	C16—C17—C18	120.05 (15)
C15—C14—H14	119.6	C16—C17—H17	120.0
C13—C14—H14	119.6	C18—C17—H17	120.0
C13—C18—C17	121.17 (14)	C17—C16—C15	119.60 (15)
C13—C18—H18	119.4	C17—C16—H16	120.2
C17—C18—H18	119.4	C15—C16—H16	120.2

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	2.08	2.9321 (16)	171
N2—H2···O2^ii	0.86	2.03	2.8838 (15)	173
C1—H1B···O1^i	0.96	2.58	3.3419 (18)	137

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