p-Anisolecarbo­nitrile

The structure of p-anisolecarbo­nitrile, C₈H₇NO, was determined by single-crystal X-ray diffraction at 100 K. It crystallizes in the monoclinic space group P2₁/c with two crystallographically independent mol­ecules in the asymmetric unit.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.115
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     -   C2      ..       7.90 su

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.725     0.970
            Tmin' and Tmax expected:      0.956     0.974
            RR' =      0.762
            Please check that your absorption correction is appropriate.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           28.30
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               3084
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3379
           Completeness (_total/calc)             91.27%
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C11    -   C12     ..       5.26 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C11    -   C12    ...       1.44 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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 (Bruker, 1997-2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

p-Anisolecarbonitrile

Crystal data

C8H7NO	F(000) = 560
Mr = 133.15	Dx = 1.297 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.5924 (7) Å	Cell parameters from 5279 reflections
b = 8.6639 (8) Å	θ = 2.6–28.3°
c = 21.7191 (19) Å	µ = 0.09 mm^−1
β = 107.396 (2)°	T = 100 K
V = 1363.3 (2) Å^3	Block, colorless
Z = 8	0.50 × 0.46 × 0.30 mm

Data collection

Bruker AXS SMART APEX CCD diffractometer	3084 independent reflections
Radiation source: fine-focus sealed tube	2818 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS in SAINT-Plus; Bruker, 1997-1999)	h = −10→9
Tmin = 0.725, Tmax = 0.97	k = −11→11
12523 measured reflections	l = −27→27

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) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0613P)^2 + 0.3082P] where P = (Fo^2 + 2Fc^2)/3
3084 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.31 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
C1	0.41852 (14)	0.32076 (13)	0.25063 (5)	0.0239 (3)
C2	0.39507 (14)	0.32069 (12)	0.31368 (5)	0.0200 (2)
C3	0.39048 (15)	0.18219 (13)	0.34590 (5)	0.0227 (2)
C4	0.36668 (14)	0.18284 (12)	0.40658 (5)	0.0218 (2)
C5	0.34752 (14)	0.32307 (12)	0.43541 (5)	0.0196 (2)
C6	0.35151 (14)	0.46203 (12)	0.40322 (5)	0.0223 (2)
C7	0.37630 (14)	0.46113 (13)	0.34312 (5)	0.0222 (2)
C8	0.34057 (17)	0.20016 (15)	0.53290 (6)	0.0309 (3)
H8A	0.2429	0.1272	0.5114	0.046*
H8B	0.3290	0.2269	0.5754	0.046*
H8C	0.4614	0.1527	0.5382	0.046*
C11	0.15365 (15)	0.71638 (13)	0.01046 (5)	0.0248 (3)
C12	0.14131 (14)	0.77237 (12)	0.07127 (5)	0.0208 (2)
C13	0.12877 (15)	0.66969 (12)	0.11939 (5)	0.0234 (3)
C14	0.11522 (14)	0.72441 (12)	0.17781 (5)	0.0216 (2)
C15	0.11236 (13)	0.88292 (12)	0.18798 (5)	0.0191 (2)
C16	0.12606 (15)	0.98575 (12)	0.13996 (5)	0.0224 (2)
C17	0.14057 (14)	0.93144 (12)	0.08229 (5)	0.0217 (2)
C18	0.09368 (16)	0.84855 (13)	0.29489 (5)	0.0246 (2)
H18A	−0.0100	0.7765	0.2804	0.037*
H18B	0.0795	0.9100	0.3310	0.037*
H18C	0.2096	0.7904	0.3089	0.037*
H3	0.4031 (18)	0.0822 (18)	0.3242 (7)	0.033 (4)*
H4	0.3606 (18)	0.0842 (17)	0.4286 (7)	0.030 (3)*
H6	0.3383 (18)	0.5572 (17)	0.4243 (7)	0.031 (3)*
H7	0.3848 (17)	0.5596 (16)	0.3211 (6)	0.028 (3)*
H13	0.1281 (18)	0.5583 (18)	0.1126 (7)	0.031 (4)*
H14	0.1059 (17)	0.6526 (15)	0.2110 (7)	0.024 (3)*
H16	0.1253 (17)	1.0930 (18)	0.1476 (6)	0.031 (3)*
H17	0.1532 (17)	1.0014 (16)	0.0494 (6)	0.024 (3)*
N1	0.43502 (14)	0.32228 (12)	0.19962 (5)	0.0311 (2)
N2	0.16209 (16)	0.67242 (12)	−0.03857 (5)	0.0336 (3)
O1	0.32373 (11)	0.33654 (9)	0.49469 (4)	0.0247 (2)
O2	0.09666 (10)	0.94893 (9)	0.24283 (3)	0.0231 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0215 (5)	0.0254 (5)	0.0237 (6)	−0.0012 (4)	0.0053 (4)	−0.0013 (4)
C2	0.0162 (5)	0.0244 (5)	0.0190 (5)	−0.0004 (4)	0.0047 (4)	−0.0013 (4)
C3	0.0238 (5)	0.0207 (5)	0.0239 (6)	0.0000 (4)	0.0075 (4)	−0.0043 (4)
C4	0.0232 (5)	0.0194 (5)	0.0230 (6)	0.0011 (4)	0.0071 (4)	0.0004 (4)
C5	0.0165 (5)	0.0247 (5)	0.0173 (5)	0.0005 (4)	0.0047 (4)	−0.0024 (4)
C6	0.0222 (5)	0.0193 (5)	0.0255 (6)	0.0004 (4)	0.0072 (4)	−0.0041 (4)
C7	0.0209 (5)	0.0206 (5)	0.0249 (6)	0.0012 (4)	0.0065 (4)	0.0010 (4)
C8	0.0371 (6)	0.0350 (6)	0.0225 (6)	0.0049 (5)	0.0118 (5)	0.0060 (5)
C11	0.0275 (5)	0.0247 (5)	0.0227 (6)	0.0000 (4)	0.0083 (4)	0.0008 (4)
C12	0.0190 (5)	0.0241 (5)	0.0192 (5)	−0.0001 (4)	0.0056 (4)	−0.0008 (4)
C13	0.0283 (6)	0.0198 (5)	0.0226 (6)	−0.0009 (4)	0.0082 (4)	−0.0012 (4)
C14	0.0247 (5)	0.0207 (5)	0.0200 (5)	−0.0019 (4)	0.0074 (4)	0.0017 (4)
C15	0.0164 (4)	0.0224 (5)	0.0180 (5)	0.0000 (4)	0.0046 (4)	−0.0014 (4)
C16	0.0262 (5)	0.0182 (5)	0.0235 (5)	−0.0005 (4)	0.0084 (4)	0.0008 (4)
C17	0.0212 (5)	0.0233 (5)	0.0208 (5)	−0.0007 (4)	0.0067 (4)	0.0029 (4)
C18	0.0298 (5)	0.0270 (5)	0.0193 (5)	0.0030 (4)	0.0108 (4)	0.0028 (4)
N1	0.0342 (5)	0.0363 (6)	0.0241 (5)	−0.0035 (4)	0.0105 (4)	−0.0023 (4)
N2	0.0455 (6)	0.0338 (6)	0.0242 (5)	0.0007 (5)	0.0143 (5)	−0.0031 (4)
O1	0.0298 (4)	0.0266 (4)	0.0188 (4)	0.0017 (3)	0.0091 (3)	−0.0012 (3)
O2	0.0315 (4)	0.0218 (4)	0.0180 (4)	0.0018 (3)	0.0104 (3)	−0.0001 (3)

Geometric parameters (Å, º)

C1—N1	1.1516 (16)	C11—N2	1.1508 (15)
C1—C2	1.4326 (15)	C11—C12	1.4361 (15)
C2—C3	1.3948 (15)	C12—C13	1.3972 (15)
C2—C7	1.4015 (15)	C12—C17	1.3990 (15)
C3—C4	1.3827 (16)	C13—C14	1.3868 (15)
C3—H3	1.004 (15)	C13—H13	0.976 (15)
C4—C5	1.3943 (15)	C14—C15	1.3922 (15)
C4—H4	0.987 (15)	C14—H14	0.971 (14)
C5—O1	1.3575 (13)	C15—O2	1.3584 (12)
C5—C6	1.3972 (15)	C15—C16	1.3990 (15)
C6—C7	1.3734 (16)	C16—C17	1.3730 (16)
C6—H6	0.963 (14)	C16—H16	0.944 (15)
C7—H7	0.990 (14)	C17—H17	0.964 (13)
C8—O1	1.4274 (14)	C18—O2	1.4320 (13)
C8—H8A	0.9800	C18—H18A	0.9800
C8—H8B	0.9800	C18—H18B	0.9800
C8—H8C	0.9800	C18—H18C	0.9800
N1—C1—C2	178.94 (12)	C13—C12—C17	119.65 (10)
C3—C2—C7	119.78 (10)	C13—C12—C11	120.70 (10)
C3—C2—C1	120.59 (10)	C17—C12—C11	119.65 (10)
C7—C2—C1	119.63 (10)	C14—C13—C12	120.46 (10)
C4—C3—C2	120.32 (10)	C14—C13—H13	118.6 (8)
C4—C3—H3	120.5 (8)	C12—C13—H13	121.0 (8)
C2—C3—H3	119.1 (8)	C13—C14—C15	119.43 (10)
C3—C4—C5	119.51 (10)	C13—C14—H14	120.2 (8)
C3—C4—H4	119.8 (8)	C15—C14—H14	120.4 (8)
C5—C4—H4	120.7 (8)	O2—C15—C14	124.34 (10)
O1—C5—C4	124.21 (10)	O2—C15—C16	115.55 (9)
O1—C5—C6	115.44 (9)	C14—C15—C16	120.11 (10)
C4—C5—C6	120.35 (10)	C17—C16—C15	120.40 (10)
C7—C6—C5	120.03 (10)	C17—C16—H16	120.3 (8)
C7—C6—H6	121.3 (8)	C15—C16—H16	119.3 (8)
C5—C6—H6	118.7 (8)	C16—C17—C12	119.94 (10)
C6—C7—C2	120.01 (10)	C16—C17—H17	120.9 (8)
C6—C7—H7	120.1 (8)	C12—C17—H17	119.1 (8)
C2—C7—H7	119.8 (8)	O2—C18—H18A	109.5
O1—C8—H8A	109.5	O2—C18—H18B	109.5
O1—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	O2—C18—H18C	109.5
O1—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5	C5—O1—C8	117.77 (9)
N2—C11—C12	179.32 (13)	C15—O2—C18	117.58 (8)