2-[(2-Chloro-3,4-dimethoxy­benzyl­idene)amino]adamantane

The title compound, C₁₉H₂₄ClNO₂, is isomeric with the 1-[(2-chloro-3,4-dimethoxy­benzyl­idene)amino]adamantane structure reported in the previous paper [Isik, Köysal, Septioglu & Çalis (2005). Acta Cryst. E61, o1851-o1852].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.125
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.80 mm
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17A   ..  CL1     ..       2.94 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14A   ..  CG1     ..       2.93 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

2-[(2-chloro-3,4-dimethoxybenzylidene)amino]adamantane

Crystal data

C19H24ClNO2	F(000) = 712
Mr = 333.86	Dx = 1.290 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12884 reflections
a = 14.2591 (11) Å	θ = 1.5–27.5°
b = 9.9334 (5) Å	µ = 0.23 mm^−1
c = 12.7325 (10) Å	T = 293 K
β = 107.610 (6)°	Prism, colourless
V = 1718.9 (2) Å^3	0.80 × 0.42 × 0.12 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	3371 independent reflections
Radiation source: fine-focus sealed tube	2604 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.5°
Ω scans	h = −17→16
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→12
Tmin = 0.898, Tmax = 0.964	l = −15→15
11934 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0763P)^2 + 0.0027P] where P = (Fo^2 + 2Fc^2)/3
3371 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.32 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
C18	0.55476 (17)	−0.0060 (2)	0.8333 (2)	0.0900 (7)
H18A	0.5152	−0.0039	0.8824	0.135*
H18B	0.6062	−0.0713	0.8589	0.135*
H18C	0.5144	−0.0299	0.7607	0.135*
C19	0.47684 (15)	0.1894 (3)	0.50040 (17)	0.0812 (6)
H19A	0.4066	0.1951	0.4835	0.122*
H19B	0.4932	0.1204	0.4561	0.122*
H19C	0.5022	0.2742	0.4851	0.122*
C2	0.75931 (12)	0.12090 (14)	0.81131 (12)	0.0469 (4)
C3	0.65787 (12)	0.12821 (15)	0.76490 (13)	0.0500 (4)
C4	0.61896 (12)	0.14685 (17)	0.65194 (14)	0.0525 (4)
C5	0.68116 (12)	0.15269 (18)	0.58674 (13)	0.0551 (4)
H5	0.6553	0.1635	0.5109	0.066*
C6	0.78099 (12)	0.14244 (16)	0.63462 (13)	0.0515 (4)
H6	0.8218	0.1456	0.5898	0.062*
C1	0.82330 (11)	0.12749 (14)	0.74744 (12)	0.0458 (3)
C7	0.93132 (12)	0.12594 (15)	0.79430 (13)	0.0484 (4)
H7	0.9600	0.1374	0.8697	0.058*
C8	1.09117 (11)	0.12276 (16)	0.78029 (12)	0.0500 (4)
H8	1.1083	0.1318	0.8605	0.060*
C15	1.12403 (12)	0.24865 (16)	0.73182 (14)	0.0562 (4)
H15	1.0900	0.3276	0.7488	0.067*
C16	1.09953 (14)	0.2341 (2)	0.60685 (15)	0.0683 (5)
H16A	1.0291	0.2236	0.5742	0.082*
H16B	1.1198	0.3145	0.5763	0.082*
C11	1.15222 (14)	0.1124 (2)	0.57975 (14)	0.0671 (5)
H11	1.1362	0.1033	0.4996	0.081*
C12	1.26289 (15)	0.1314 (2)	0.63010 (16)	0.0707 (5)
H12A	1.2838	0.2116	0.5999	0.085*
H12B	1.2974	0.0548	0.6121	0.085*
C13	1.28809 (13)	0.14467 (19)	0.75510 (15)	0.0591 (4)
H13	1.3593	0.1559	0.7875	0.071*
C17	1.25487 (13)	0.01895 (18)	0.80195 (15)	0.0611 (4)
H17A	1.2712	0.0269	0.8814	0.073*
H17B	1.2888	−0.0591	0.7855	0.073*
C9	1.14378 (12)	0.00101 (16)	0.75171 (13)	0.0528 (4)
H9	1.1229	−0.0804	0.7820	0.063*
C10	1.11964 (14)	−0.01339 (19)	0.62733 (15)	0.0627 (4)
H10A	1.1531	−0.0915	0.6102	0.075*
H10B	1.0494	−0.0263	0.5947	0.075*
C14	1.23511 (13)	0.26620 (18)	0.78330 (16)	0.0633 (5)
H14A	1.2566	0.3475	0.7552	0.076*
H14B	1.2508	0.2746	0.8626	0.076*
N1	0.98483 (10)	0.10937 (14)	0.73346 (11)	0.0556 (3)
O1	0.59689 (10)	0.12317 (13)	0.83040 (11)	0.0659 (3)
O2	0.51893 (9)	0.15739 (14)	0.61334 (11)	0.0691 (4)
Cl1	0.80551 (3)	0.09987 (5)	0.95260 (3)	0.06582 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C18	0.0842 (16)	0.0892 (16)	0.1184 (19)	0.0063 (12)	0.0630 (14)	0.0251 (13)
C19	0.0557 (10)	0.1124 (18)	0.0682 (12)	0.0091 (11)	0.0076 (8)	0.0123 (11)
C2	0.0554 (9)	0.0429 (8)	0.0446 (8)	0.0022 (6)	0.0184 (6)	−0.0010 (6)
C3	0.0538 (9)	0.0489 (8)	0.0539 (8)	0.0026 (7)	0.0261 (7)	−0.0007 (6)
C4	0.0459 (8)	0.0553 (9)	0.0571 (9)	−0.0002 (7)	0.0168 (7)	0.0003 (7)
C5	0.0509 (9)	0.0686 (10)	0.0449 (8)	−0.0037 (8)	0.0130 (7)	0.0015 (7)
C6	0.0510 (9)	0.0594 (9)	0.0475 (8)	−0.0054 (7)	0.0199 (7)	−0.0008 (6)
C1	0.0485 (8)	0.0418 (7)	0.0478 (8)	−0.0023 (6)	0.0157 (6)	−0.0019 (6)
C7	0.0500 (9)	0.0477 (8)	0.0459 (8)	−0.0012 (7)	0.0122 (6)	−0.0010 (6)
C8	0.0426 (8)	0.0611 (9)	0.0433 (8)	−0.0027 (7)	0.0086 (6)	−0.0018 (6)
C15	0.0464 (8)	0.0449 (8)	0.0720 (10)	0.0011 (7)	0.0101 (7)	−0.0016 (7)
C16	0.0564 (10)	0.0715 (12)	0.0702 (11)	−0.0042 (9)	0.0088 (8)	0.0272 (9)
C11	0.0656 (11)	0.0900 (14)	0.0458 (9)	−0.0098 (10)	0.0169 (8)	0.0012 (8)
C12	0.0635 (11)	0.0857 (13)	0.0696 (12)	−0.0067 (10)	0.0303 (9)	0.0016 (9)
C13	0.0417 (8)	0.0660 (10)	0.0666 (10)	−0.0012 (8)	0.0120 (7)	−0.0016 (8)
C17	0.0542 (10)	0.0606 (10)	0.0641 (10)	0.0115 (8)	0.0112 (7)	0.0079 (8)
C9	0.0562 (9)	0.0435 (8)	0.0572 (9)	−0.0014 (7)	0.0148 (7)	0.0065 (6)
C10	0.0627 (11)	0.0610 (10)	0.0635 (10)	−0.0070 (8)	0.0177 (8)	−0.0157 (8)
C14	0.0508 (9)	0.0538 (10)	0.0804 (12)	−0.0078 (8)	0.0126 (8)	−0.0066 (8)
N1	0.0449 (7)	0.0703 (9)	0.0507 (7)	−0.0061 (6)	0.0131 (6)	−0.0036 (6)
O1	0.0650 (8)	0.0753 (8)	0.0699 (8)	0.0084 (6)	0.0393 (6)	0.0034 (6)
O2	0.0453 (6)	0.0960 (10)	0.0649 (8)	0.0052 (6)	0.0151 (5)	0.0083 (6)
Cl1	0.0742 (3)	0.0807 (3)	0.0447 (2)	0.0086 (2)	0.02106 (19)	0.00249 (18)

Geometric parameters (Å, º)

C18—O1	1.422 (2)	C8—H8	0.9800
C18—H18A	0.9600	C15—C16	1.529 (2)
C18—H18B	0.9600	C15—C14	1.530 (2)
C18—H18C	0.9600	C15—H15	0.9800
C19—O2	1.417 (2)	C16—C11	1.517 (3)
C19—H19A	0.9600	C16—H16A	0.9700
C19—H19B	0.9600	C16—H16B	0.9700
C19—H19C	0.9600	C11—C10	1.522 (3)
C2—C3	1.389 (2)	C11—C12	1.525 (3)
C2—C1	1.395 (2)	C11—H11	0.9800
C2—Cl1	1.7310 (15)	C12—C13	1.528 (3)
C3—O1	1.3759 (18)	C12—H12A	0.9700
C3—C4	1.389 (2)	C12—H12B	0.9700
C4—O2	1.365 (2)	C13—C17	1.520 (3)
C4—C5	1.387 (2)	C13—C14	1.523 (3)
C5—C6	1.372 (2)	C13—H13	0.9800
C5—H5	0.9300	C17—C9	1.529 (2)
C6—C1	1.388 (2)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C1—C7	1.474 (2)	C9—C10	1.522 (2)
C7—N1	1.252 (2)	C9—H9	0.9800
C7—H7	0.9300	C10—H10A	0.9700
C8—N1	1.458 (2)	C10—H10B	0.9700
C8—C9	1.524 (2)	C14—H14A	0.9700
C8—C15	1.529 (2)	C14—H14B	0.9700
O1—C18—H18A	109.5	C11—C16—H16B	109.7
O1—C18—H18B	109.5	C15—C16—H16B	109.7
H18A—C18—H18B	109.5	H16A—C16—H16B	108.2
O1—C18—H18C	109.5	C16—C11—C10	109.39 (15)
H18A—C18—H18C	109.5	C16—C11—C12	109.08 (16)
H18B—C18—H18C	109.5	C10—C11—C12	109.62 (16)
O2—C19—H19A	109.5	C16—C11—H11	109.6
O2—C19—H19B	109.5	C10—C11—H11	109.6
H19A—C19—H19B	109.5	C12—C11—H11	109.6
O2—C19—H19C	109.5	C11—C12—C13	109.64 (14)
H19A—C19—H19C	109.5	C11—C12—H12A	109.7
H19B—C19—H19C	109.5	C13—C12—H12A	109.7
C3—C2—C1	122.00 (14)	C11—C12—H12B	109.7
C3—C2—Cl1	117.92 (11)	C13—C12—H12B	109.7
C1—C2—Cl1	120.06 (13)	H12A—C12—H12B	108.2
O1—C3—C4	120.33 (15)	C17—C13—C14	108.84 (15)
O1—C3—C2	120.53 (15)	C17—C13—C12	109.55 (15)
C4—C3—C2	119.07 (14)	C14—C13—C12	109.69 (15)
O2—C4—C5	124.68 (15)	C17—C13—H13	109.6
O2—C4—C3	115.45 (14)	C14—C13—H13	109.6
C5—C4—C3	119.87 (15)	C12—C13—H13	109.6
C6—C5—C4	119.74 (15)	C13—C17—C9	109.76 (13)
C6—C5—H5	120.1	C13—C17—H17A	109.7
C4—C5—H5	120.1	C9—C17—H17A	109.7
C5—C6—C1	122.38 (15)	C13—C17—H17B	109.7
C5—C6—H6	118.8	C9—C17—H17B	109.7
C1—C6—H6	118.8	H17A—C17—H17B	108.2
C6—C1—C2	116.89 (15)	C10—C9—C8	110.50 (13)
C6—C1—C7	119.60 (14)	C10—C9—C17	109.01 (14)
C2—C1—C7	123.44 (14)	C8—C9—C17	109.28 (13)
N1—C7—C1	120.58 (14)	C10—C9—H9	109.3
N1—C7—H7	119.7	C8—C9—H9	109.3
C1—C7—H7	119.7	C17—C9—H9	109.3
N1—C8—C9	110.86 (13)	C11—C10—C9	109.69 (13)
N1—C8—C15	108.50 (13)	C11—C10—H10A	109.7
C9—C8—C15	108.64 (13)	C9—C10—H10A	109.7
N1—C8—H8	109.6	C11—C10—H10B	109.7
C9—C8—H8	109.6	C9—C10—H10B	109.7
C15—C8—H8	109.6	H10A—C10—H10B	108.2
C16—C15—C8	109.94 (13)	C13—C14—C15	109.38 (14)
C16—C15—C14	109.72 (15)	C13—C14—H14A	109.8
C8—C15—C14	108.91 (13)	C15—C14—H14A	109.8
C16—C15—H15	109.4	C13—C14—H14B	109.8
C8—C15—H15	109.4	C15—C14—H14B	109.8
C14—C15—H15	109.4	H14A—C14—H14B	108.2
C11—C16—C15	109.83 (14)	C7—N1—C8	119.22 (14)
C11—C16—H16A	109.7	C3—O1—C18	113.47 (14)
C15—C16—H16A	109.7	C4—O2—C19	117.28 (14)
C1—C2—C3—O1	−179.14 (14)	C16—C11—C12—C13	60.43 (19)
Cl1—C2—C3—O1	2.1 (2)	C10—C11—C12—C13	−59.3 (2)
C1—C2—C3—C4	−2.0 (2)	C11—C12—C13—C17	59.2 (2)
Cl1—C2—C3—C4	179.15 (12)	C11—C12—C13—C14	−60.2 (2)
O1—C3—C4—O2	−0.8 (2)	C14—C13—C17—C9	60.16 (19)
C2—C3—C4—O2	−177.93 (14)	C12—C13—C17—C9	−59.78 (19)
O1—C3—C4—C5	179.56 (15)	N1—C8—C9—C10	59.93 (16)
C2—C3—C4—C5	2.5 (2)	C15—C8—C9—C10	−59.21 (16)
O2—C4—C5—C6	179.26 (16)	N1—C8—C9—C17	179.88 (13)
C3—C4—C5—C6	−1.2 (3)	C15—C8—C9—C17	60.74 (16)
C4—C5—C6—C1	−0.6 (3)	C13—C17—C9—C10	60.22 (18)
C5—C6—C1—C2	1.1 (2)	C13—C17—C9—C8	−60.63 (18)
C5—C6—C1—C7	−176.03 (15)	C16—C11—C10—C9	−59.42 (19)
C3—C2—C1—C6	0.3 (2)	C12—C11—C10—C9	60.13 (19)
Cl1—C2—C1—C6	179.08 (11)	C8—C9—C10—C11	59.84 (19)
C3—C2—C1—C7	177.27 (14)	C17—C9—C10—C11	−60.27 (18)
Cl1—C2—C1—C7	−4.0 (2)	C17—C13—C14—C15	−60.64 (19)
C6—C1—C7—N1	−15.2 (2)	C12—C13—C14—C15	59.21 (19)
C2—C1—C7—N1	167.95 (15)	C16—C15—C14—C13	−58.90 (19)
N1—C8—C15—C16	−61.58 (17)	C8—C15—C14—C13	61.48 (19)
C9—C8—C15—C16	59.02 (16)	C1—C7—N1—C8	173.44 (14)
N1—C8—C15—C14	178.17 (13)	C9—C8—N1—C7	129.10 (15)
C9—C8—C15—C14	−61.23 (17)	C15—C8—N1—C7	−111.68 (16)
C8—C15—C16—C11	−60.00 (18)	C4—C3—O1—C18	83.2 (2)
C14—C15—C16—C11	59.76 (18)	C2—C3—O1—C18	−99.71 (19)
C15—C16—C11—C10	59.67 (19)	C5—C4—O2—C19	−6.3 (3)
C15—C16—C11—C12	−60.22 (18)	C3—C4—O2—C19	174.08 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···Cl1^i	0.97	2.94	3.6784 (19)	134
C14—H14A···Cg1^ii	0.97	2.93	3.7274 (19)	141

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