9-Chloro-10-(di­methoxy­methyl)­anthracene

In the title compound, C₁₇H₁₅ClO₂, the anthracene ring system is planar and the bond lengths and angles are unexceptional. In the crystal structure, the mol­ecules stack along the a axis and there are no significantly short intermolecular contacts.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.071
• wR factor = 0.255
• Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.255
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.28
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT391_ALERT_3_C Deviating Methyl C16     H-C-H Bond Angle ......     100.00 Deg.
PLAT410_ALERT_2_C Short Intra H...H Contact  H1     ..  H2      ..       1.97 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.97(4), Rep   0.966(19) ......       2.11 su-Rat
              C1   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.99(4), Rep   0.993(19) ......       2.11 su-Rat
              C4   -H2      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.96(4), Rep   0.963(19) ......       2.11 su-Rat
              C5   -H3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.97(4), Rep   0.968(19) ......       2.11 su-Rat
              C6   -H4      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.96(4), Rep   0.965(19) ......       2.11 su-Rat
              C12  -H7      1.555   1.555

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

   6 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
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

9-Chloro-10-(dimethoxymethyl)anthracene

Crystal data

C17H15ClO2	Dx = 1.308 Mg m^−3
Mr = 286.74	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 1879 reflections
a = 10.553 (12) Å	θ = 2.3–20.1°
b = 8.948 (10) Å	µ = 0.26 mm^−1
c = 30.84 (3) Å	T = 293 K
V = 2912 (6) Å^3	Block, colourless
Z = 8	0.42 × 0.35 × 0.28 mm
F(000) = 1200

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2550 independent reflections
Radiation source: fine-focus sealed tube	1069 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.087
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.899, Tmax = 0.931	k = −10→10
13634 measured reflections	l = −36→25

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.255	All H-atom parameters refined
S = 0.95	w = 1/[σ^2(Fo^2) + (0.141P)^2] where P = (Fo^2 + 2Fc^2)/3
2550 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.78 e Å^−3
24 restraints	Δρmin = −0.24 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
Cl1	0.70960 (15)	−0.00737 (19)	0.33802 (5)	0.0968 (7)
O1	0.2791 (3)	0.4429 (4)	0.42295 (12)	0.0743 (11)
O2	0.4232 (4)	0.6173 (4)	0.40408 (12)	0.0875 (12)
C1	0.3557 (5)	0.4899 (6)	0.38927 (18)	0.0701 (15)
C2	0.4426 (4)	0.3651 (6)	0.37604 (15)	0.0608 (13)
C3	0.4317 (5)	0.2951 (6)	0.33597 (15)	0.0638 (13)
C4	0.3320 (6)	0.3339 (8)	0.3053 (2)	0.0897 (19)
C5	0.3213 (7)	0.2591 (10)	0.2672 (2)	0.100 (2)
C6	0.4044 (9)	0.1453 (10)	0.2562 (2)	0.112 (2)
C7	0.4982 (7)	0.1059 (8)	0.28245 (19)	0.0894 (18)
C8	0.5150 (5)	0.1770 (6)	0.32365 (15)	0.0663 (14)
C9	0.6082 (4)	0.1346 (6)	0.35240 (16)	0.0649 (14)
C10	0.6225 (4)	0.2002 (5)	0.39319 (15)	0.0600 (13)
C11	0.7172 (5)	0.1546 (7)	0.42283 (19)	0.0770 (16)
C12	0.7228 (5)	0.2148 (8)	0.4626 (2)	0.0865 (18)
C13	0.6372 (6)	0.3229 (7)	0.47582 (19)	0.0873 (18)
C14	0.5482 (5)	0.3710 (6)	0.44869 (16)	0.0664 (14)
C15	0.5364 (4)	0.3150 (5)	0.40588 (14)	0.0565 (12)
C16	0.1691 (6)	0.5331 (7)	0.4297 (2)	0.0943 (19)
C17	0.4658 (6)	0.7057 (8)	0.3707 (2)	0.110 (2)
H1	0.303 (4)	0.524 (5)	0.3655 (11)	0.080*
H2	0.274 (4)	0.419 (4)	0.3101 (15)	0.080*
H3	0.254 (3)	0.311 (5)	0.2526 (14)	0.080*
H4	0.398 (4)	0.087 (5)	0.2298 (11)	0.080*
H5	0.548 (4)	0.016 (4)	0.2743 (16)	0.080*
H6	0.765 (4)	0.066 (4)	0.4162 (14)	0.080*
H7	0.794 (3)	0.194 (5)	0.4811 (13)	0.080*
H8	0.637 (5)	0.370 (5)	0.5045 (9)	0.080*
H9	0.493 (4)	0.456 (4)	0.4550 (15)	0.080*
H10	0.105 (3)	0.493 (4)	0.4536 (9)	0.080*
H11	0.194 (4)	0.628 (3)	0.4387 (11)	0.080*
H12	0.114 (4)	0.535 (4)	0.4045 (8)	0.080*
H13	0.518 (3)	0.787 (3)	0.3830 (9)	0.080*
H14	0.528 (3)	0.646 (3)	0.3536 (8)	0.080*
H15	0.404 (2)	0.743 (3)	0.3522 (8)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0956 (13)	0.1004 (13)	0.0945 (12)	0.0139 (9)	0.0212 (9)	−0.0150 (8)
O1	0.055 (2)	0.077 (3)	0.091 (3)	0.0130 (18)	0.0040 (18)	0.0096 (19)
O2	0.104 (3)	0.060 (2)	0.098 (3)	0.002 (2)	−0.001 (2)	0.003 (2)
C1	0.072 (4)	0.064 (4)	0.074 (4)	0.006 (3)	−0.007 (3)	0.014 (3)
C2	0.060 (3)	0.063 (3)	0.059 (3)	−0.009 (3)	−0.004 (2)	0.009 (2)
C3	0.063 (3)	0.073 (4)	0.055 (3)	−0.009 (3)	−0.001 (2)	0.016 (3)
C4	0.086 (5)	0.107 (5)	0.076 (4)	−0.018 (4)	−0.016 (3)	0.021 (4)
C5	0.108 (6)	0.132 (7)	0.061 (4)	−0.026 (5)	−0.021 (4)	0.023 (4)
C6	0.134 (7)	0.143 (7)	0.058 (4)	−0.039 (6)	−0.004 (5)	−0.007 (4)
C7	0.111 (5)	0.099 (5)	0.058 (4)	−0.020 (4)	0.002 (3)	−0.001 (3)
C8	0.071 (3)	0.073 (4)	0.055 (3)	−0.015 (3)	0.009 (3)	0.004 (3)
C9	0.056 (3)	0.073 (4)	0.066 (3)	0.000 (3)	0.016 (3)	0.004 (3)
C10	0.057 (3)	0.061 (3)	0.062 (3)	−0.003 (3)	0.003 (2)	0.002 (2)
C11	0.063 (4)	0.089 (4)	0.079 (4)	0.023 (3)	−0.002 (3)	0.003 (3)
C12	0.073 (4)	0.111 (5)	0.076 (4)	0.024 (4)	−0.021 (3)	−0.002 (3)
C13	0.080 (4)	0.110 (5)	0.071 (4)	0.016 (4)	−0.017 (3)	−0.017 (3)
C14	0.064 (3)	0.069 (4)	0.065 (3)	0.003 (3)	−0.004 (3)	−0.003 (3)
C15	0.054 (3)	0.058 (3)	0.057 (3)	−0.001 (2)	−0.001 (2)	0.006 (2)
C16	0.066 (4)	0.084 (5)	0.133 (6)	0.029 (3)	−0.017 (4)	0.003 (4)
C17	0.094 (5)	0.093 (5)	0.144 (6)	−0.003 (4)	0.004 (4)	0.036 (5)

Geometric parameters (Å, º)

Cl1—C9	1.719 (5)	C8—C9	1.378 (7)
O1—C1	1.382 (6)	C9—C10	1.396 (7)
O1—C16	1.429 (6)	C10—C11	1.414 (7)
O2—C17	1.374 (7)	C10—C15	1.427 (6)
O2—C1	1.419 (6)	C11—C12	1.340 (8)
C1—C2	1.501 (7)	C11—H6	0.96 (2)
C1—H1	0.966 (19)	C12—C13	1.385 (8)
C2—C3	1.390 (7)	C12—H7	0.965 (19)
C2—C15	1.424 (6)	C13—C14	1.329 (7)
C3—C8	1.426 (7)	C13—H8	0.978 (19)
C3—C4	1.458 (7)	C14—C15	1.417 (6)
C4—C5	1.356 (9)	C14—H9	0.97 (2)
C4—H2	0.993 (19)	C16—H10	1.063 (18)
C5—C6	1.386 (10)	C16—H11	0.931 (18)
C5—H3	0.963 (19)	C16—H12	0.968 (18)
C6—C7	1.327 (10)	C17—H13	0.988 (16)
C6—H4	0.968 (19)	C17—H14	1.002 (16)
C7—C8	1.432 (8)	C17—H15	0.927 (15)
C7—H5	0.99 (2)
C1—O1—C16	114.4 (4)	C10—C9—Cl1	118.4 (4)
C17—O2—C1	112.7 (5)	C9—C10—C11	122.5 (5)
O1—C1—O2	107.2 (4)	C9—C10—C15	118.8 (4)
O1—C1—C2	109.6 (4)	C11—C10—C15	118.7 (5)
O2—C1—C2	112.2 (4)	C12—C11—C10	120.4 (5)
O1—C1—H1	109 (3)	C12—C11—H6	120 (3)
O2—C1—H1	106 (3)	C10—C11—H6	118 (3)
C2—C1—H1	112 (3)	C11—C12—C13	121.4 (5)
C3—C2—C15	119.3 (5)	C11—C12—H7	120 (3)
C3—C2—C1	121.8 (4)	C13—C12—H7	118 (3)
C15—C2—C1	118.9 (4)	C14—C13—C12	120.1 (5)
C2—C3—C8	121.4 (5)	C14—C13—H8	116 (3)
C2—C3—C4	122.0 (5)	C12—C13—H8	124 (3)
C8—C3—C4	116.6 (5)	C13—C14—C15	122.3 (5)
C5—C4—C3	120.3 (7)	C13—C14—H9	123 (3)
C5—C4—H2	117 (3)	C15—C14—H9	114 (3)
C3—C4—H2	122 (3)	C14—C15—C2	123.5 (5)
C4—C5—C6	121.5 (7)	C14—C15—C10	117.0 (4)
C4—C5—H3	103 (3)	C2—C15—C10	119.5 (4)
C6—C5—H3	135 (3)	O1—C16—H10	115 (3)
C7—C6—C5	121.2 (7)	O1—C16—H11	109 (3)
C7—C6—H4	115 (3)	H10—C16—H11	106 (2)
C5—C6—H4	124 (3)	O1—C16—H12	112 (3)
C6—C7—C8	121.1 (7)	H10—C16—H12	100 (2)
C6—C7—H5	117 (3)	H11—C16—H12	113 (3)
C8—C7—H5	121 (3)	O2—C17—H13	108.7 (17)
C9—C8—C3	118.2 (5)	O2—C17—H14	107.6 (16)
C9—C8—C7	122.5 (6)	H13—C17—H14	104 (2)
C3—C8—C7	119.3 (5)	O2—C17—H15	116.3 (18)
C8—C9—C10	122.7 (5)	H13—C17—H15	111 (2)
C8—C9—Cl1	118.8 (4)	H14—C17—H15	109 (2)