2-(4-Chloro­phenyl)-5-methyl-6,7,8,9,10,11-hexa­hydro­cyclo­octa­[e][1,3]­oxazolo­[3,2-a]­pyridin-12-ium perchlorate

The title compound, C₂₀H₂₁ClNO⁺·ClO₄^-, was synthesized and characterized by ¹H NMR and X-ray diffraction techniques.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.124
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.58 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       5.33 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20     ..       5.64 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       6.17 su
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        Cl2

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C20 H21 Cl2 N1 O5
            Atom count from _chemical_formula_moiety:C20 H21 Cl2 N1 O2

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

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

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

2-(4-Chlorophenyl)-5-methyl-6,7,8,9,10,11- hexahydrocycloocta[e][1,3]oxazolo[3,2-a]pyridin-12-ium perchlorate

Crystal data

C20H21ClNO^+·ClO^4^−	F(000) = 888
Mr = 426.28	Dx = 1.431 Mg m^−3
Monoclinic, P21/c	Melting point: 584 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54180 Å
a = 7.8301 (9) Å	Cell parameters from 25 reflections
b = 18.6827 (19) Å	θ = 30–34°
c = 13.8840 (14) Å	µ = 3.23 mm^−1
β = 103.013 (9)°	T = 293 K
V = 1978.9 (4) Å^3	Prism, colourless
Z = 4	0.26 × 0.24 × 0.21 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: Enraf–Nonius FR590	θmax = 74.9°, θmin = 4.0°
Graphite monochromator	h = −9→9
non–profiled ω/2τ scans	k = 0→23
3977 measured reflections	l = 0→17
3977 independent reflections	1 standard reflections every 60 min
2581 reflections with I > 2σ(I)	intensity decay: 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.93	w = 1/[σ^2(Fo^2) + (0.0584P)^2], where P = (Fo^2 + 2Fc^2)/3
3977 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.20 e Å^−3
1 restraint	Δρmin = −0.16 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	−0.34369 (10)	1.00880 (5)	0.91991 (6)	0.0888 (3)
N1	0.5028 (2)	0.86720 (10)	0.72782 (14)	0.0503 (4)
C2	0.3696 (3)	0.85949 (13)	0.78085 (18)	0.0554 (6)
H2	0.3506	0.8198	0.8174	0.067*
C3	0.2770 (3)	0.91938 (13)	0.76874 (18)	0.0534 (6)
O4	0.3410 (2)	0.96593 (8)	0.70786 (13)	0.0560 (4)
C5	0.4801 (3)	0.93251 (13)	0.68388 (18)	0.0523 (5)
C6	0.5839 (4)	0.95713 (14)	0.62524 (19)	0.0633 (7)
H6	0.5659	1.0021	0.5960	0.076*
C7	0.7189 (4)	0.91271 (15)	0.61006 (19)	0.0613 (6)
C8	0.7439 (4)	0.84640 (15)	0.65768 (18)	0.0607 (6)
C9	0.6388 (3)	0.82224 (14)	0.71675 (18)	0.0569 (6)
C10	0.8246 (4)	0.93784 (16)	0.5396 (2)	0.0781 (9)
H10A	0.8065	0.9882	0.5282	0.117*
H10B	0.7888	0.9126	0.4781	0.117*
H10C	0.9466	0.9289	0.5671	0.117*
C11	0.8922 (4)	0.79813 (17)	0.6436 (2)	0.0719 (8)
H11A	0.9310	0.7691	0.7024	0.086*
H11B	0.9902	0.8275	0.6356	0.086*
C12	0.8384 (4)	0.74893 (18)	0.5539 (2)	0.0808 (9)
H12A	0.8192	0.7780	0.4946	0.097*
H12B	0.9352	0.7168	0.5524	0.097*
C13	0.6769 (5)	0.7047 (2)	0.5508 (3)	0.0981 (11)
H13A	0.5765	0.7365	0.5398	0.118*
H13B	0.6612	0.6727	0.4944	0.118*
C14	0.6771 (6)	0.66256 (17)	0.6375 (4)	0.1094 (13)
H14A	0.7982	0.6558	0.6722	0.131*
H14B	0.6306	0.6157	0.6157	0.131*
C15	0.5744 (5)	0.69086 (16)	0.7139 (3)	0.1026 (12)
H15A	0.4567	0.7036	0.6788	0.123*
H15B	0.5645	0.6524	0.7592	0.123*
C16	0.6551 (4)	0.75408 (16)	0.7727 (2)	0.0809 (8)
H16A	0.6007	0.7600	0.8284	0.097*
H16B	0.7785	0.7443	0.7989	0.097*
C17	0.1262 (3)	0.94248 (13)	0.80539 (18)	0.0527 (5)
C18	0.0419 (4)	1.00617 (14)	0.7757 (2)	0.0633 (7)
H18	0.0837	1.0351	0.7316	0.076*
C19	−0.1023 (4)	1.02839 (15)	0.8091 (2)	0.0675 (7)
H19	−0.1594	1.0709	0.7869	0.081*
C20	−0.1593 (3)	0.98537 (17)	0.8767 (2)	0.0674 (7)
C21	−0.0754 (4)	0.92228 (17)	0.9097 (2)	0.0736 (8)
H21	−0.1154	0.8942	0.9554	0.088*
C22	0.0682 (4)	0.90099 (15)	0.8749 (2)	0.0654 (7)
H22	0.1263	0.8588	0.8979	0.079*
Cl2	0.22564 (9)	0.66938 (3)	0.92960 (5)	0.06249 (18)
O21	0.2390 (4)	0.66159 (19)	1.03088 (19)	0.1434 (13)
O22	0.0624 (4)	0.6417 (2)	0.8795 (3)	0.1717 (16)
O23	0.2310 (5)	0.74037 (17)	0.9149 (3)	0.1857 (17)
O24	0.3728 (5)	0.6382 (2)	0.9031 (3)	0.1652 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0607 (4)	0.1184 (7)	0.0924 (5)	0.0066 (4)	0.0277 (4)	−0.0219 (5)
N1	0.0486 (11)	0.0504 (10)	0.0528 (11)	0.0002 (8)	0.0130 (9)	−0.0009 (9)
C2	0.0537 (14)	0.0579 (13)	0.0569 (13)	−0.0063 (11)	0.0171 (11)	0.0036 (12)
C3	0.0454 (13)	0.0592 (14)	0.0586 (13)	−0.0031 (10)	0.0178 (10)	0.0019 (12)
O4	0.0530 (10)	0.0557 (9)	0.0640 (10)	−0.0012 (7)	0.0233 (8)	0.0024 (8)
C5	0.0535 (13)	0.0509 (12)	0.0562 (12)	−0.0060 (10)	0.0202 (11)	−0.0035 (11)
C6	0.0736 (18)	0.0584 (15)	0.0619 (14)	−0.0062 (13)	0.0238 (13)	−0.0031 (13)
C7	0.0696 (17)	0.0627 (15)	0.0562 (13)	−0.0159 (13)	0.0241 (12)	−0.0146 (13)
C8	0.0613 (16)	0.0721 (17)	0.0499 (12)	−0.0025 (12)	0.0150 (11)	−0.0134 (13)
C9	0.0528 (15)	0.0649 (15)	0.0519 (12)	0.0002 (11)	0.0098 (11)	−0.0034 (12)
C10	0.084 (2)	0.083 (2)	0.0792 (19)	−0.0084 (17)	0.0436 (17)	−0.0030 (17)
C11	0.0544 (16)	0.093 (2)	0.0694 (17)	0.0025 (15)	0.0159 (13)	−0.0125 (16)
C12	0.079 (2)	0.087 (2)	0.084 (2)	−0.0060 (17)	0.0334 (17)	−0.0266 (18)
C13	0.078 (2)	0.101 (3)	0.114 (3)	−0.009 (2)	0.019 (2)	−0.033 (2)
C14	0.131 (3)	0.063 (2)	0.146 (4)	0.001 (2)	0.056 (3)	−0.006 (2)
C15	0.130 (3)	0.0634 (17)	0.127 (3)	−0.0018 (19)	0.054 (3)	0.0243 (17)
C16	0.089 (2)	0.0842 (18)	0.0748 (19)	0.0195 (16)	0.0290 (16)	0.0247 (15)
C17	0.0425 (12)	0.0596 (14)	0.0584 (13)	−0.0007 (10)	0.0167 (10)	−0.0093 (12)
C18	0.0689 (18)	0.0611 (15)	0.0648 (15)	−0.0030 (13)	0.0249 (13)	−0.0056 (13)
C19	0.0683 (18)	0.0631 (16)	0.0719 (16)	0.0065 (13)	0.0178 (14)	−0.0050 (14)
C20	0.0502 (15)	0.086 (2)	0.0642 (15)	0.0049 (14)	0.0099 (12)	−0.0158 (15)
C21	0.0631 (18)	0.093 (2)	0.0692 (17)	−0.0117 (16)	0.0241 (14)	0.0009 (17)
C22	0.0707 (18)	0.0570 (14)	0.0745 (17)	0.0073 (13)	0.0288 (14)	0.0093 (14)
Cl2	0.0703 (4)	0.0549 (3)	0.0664 (4)	0.0012 (3)	0.0240 (3)	0.0039 (3)
O21	0.113 (2)	0.245 (4)	0.0742 (15)	0.044 (2)	0.0253 (15)	0.036 (2)
O22	0.139 (3)	0.225 (4)	0.157 (3)	−0.082 (3)	0.046 (2)	−0.086 (3)
O23	0.183 (4)	0.091 (2)	0.278 (5)	−0.005 (2)	0.040 (3)	0.052 (3)
O24	0.166 (3)	0.184 (3)	0.173 (3)	0.052 (3)	0.097 (3)	−0.016 (3)

Geometric parameters (Å, º)

Cl1—C20	1.740 (3)	C13—C14	1.439 (5)
N1—C5	1.358 (3)	C13—H13A	0.9700
N1—C9	1.392 (3)	C13—H13B	0.9700
N1—C2	1.413 (3)	C14—C15	1.560 (5)
C2—C3	1.323 (3)	C14—H14A	0.9700
C2—H2	0.9300	C14—H14B	0.9700
C3—O4	1.383 (3)	C15—C16	1.493 (4)
C3—C17	1.453 (3)	C15—H15A	0.9700
O4—C5	1.360 (3)	C15—H15B	0.9700
C5—C6	1.354 (3)	C16—H16A	0.9700
C6—C7	1.397 (4)	C16—H16B	0.9700
C6—H6	0.9300	C17—C18	1.378 (3)
C7—C8	1.397 (4)	C17—C22	1.392 (3)
C7—C10	1.493 (3)	C18—C19	1.377 (4)
C8—C9	1.363 (4)	C18—H18	0.9300
C8—C11	1.517 (4)	C19—C20	1.384 (4)
C9—C16	1.482 (4)	C19—H19	0.9300
C10—H10A	0.9600	C20—C21	1.377 (4)
C10—H10B	0.9600	C21—C22	1.378 (4)
C10—H10C	0.9600	C21—H21	0.9300
C11—C12	1.529 (4)	C22—H22	0.9300
C11—H11A	0.9700	Cl2—O23	1.344 (3)
C11—H11B	0.9700	Cl2—O21	1.394 (3)
C12—C13	1.503 (4)	Cl2—O22	1.409 (3)
C12—H12A	0.9700	Cl2—O24	1.412 (3)
C12—H12B	0.9700
C5—N1—C9	121.2 (2)	C14—C13—H13B	108.3
C5—N1—C2	106.75 (19)	C12—C13—H13B	108.3
C9—N1—C2	132.0 (2)	H13A—C13—H13B	107.4
C3—C2—N1	107.2 (2)	C13—C14—C15	118.7 (3)
C3—C2—H2	126.4	C13—C14—H14A	107.6
N1—C2—H2	126.4	C15—C14—H14A	107.6
C2—C3—O4	110.2 (2)	C13—C14—H14B	107.6
C2—C3—C17	132.2 (2)	C15—C14—H14B	107.6
O4—C3—C17	117.5 (2)	H14A—C14—H14B	107.1
C5—O4—C3	106.34 (18)	C16—C15—C14	114.9 (3)
C6—C5—N1	122.7 (2)	C16—C15—H15A	108.6
C6—C5—O4	127.8 (2)	C14—C15—H15A	108.6
N1—C5—O4	109.50 (19)	C16—C15—H15B	108.6
C5—C6—C7	117.8 (3)	C14—C15—H15B	108.6
C5—C6—H6	121.1	H15A—C15—H15B	107.5
C7—C6—H6	121.1	C9—C16—C15	114.7 (3)
C6—C7—C8	119.1 (2)	C9—C16—H16A	108.6
C6—C7—C10	117.5 (3)	C15—C16—H16A	108.6
C8—C7—C10	123.4 (3)	C9—C16—H16B	108.6
C9—C8—C7	122.6 (3)	C15—C16—H16B	108.6
C9—C8—C11	117.7 (3)	H16A—C16—H16B	107.6
C7—C8—C11	119.7 (2)	C18—C17—C22	118.6 (2)
C8—C9—N1	116.6 (2)	C18—C17—C3	121.6 (2)
C8—C9—C16	127.4 (3)	C22—C17—C3	119.7 (2)
N1—C9—C16	116.0 (2)	C19—C18—C17	122.2 (3)
C7—C10—H10A	109.5	C19—C18—H18	118.9
C7—C10—H10B	109.5	C17—C18—H18	118.9
H10A—C10—H10B	109.5	C18—C19—C20	117.8 (3)
C7—C10—H10C	109.5	C18—C19—H19	121.1
H10A—C10—H10C	109.5	C20—C19—H19	121.1
H10B—C10—H10C	109.5	C21—C20—C19	121.4 (3)
C8—C11—C12	112.6 (2)	C21—C20—Cl1	118.1 (2)
C8—C11—H11A	109.1	C19—C20—Cl1	120.5 (2)
C12—C11—H11A	109.1	C20—C21—C22	119.7 (3)
C8—C11—H11B	109.1	C20—C21—H21	120.2
C12—C11—H11B	109.1	C22—C21—H21	120.2
H11A—C11—H11B	107.8	C21—C22—C17	120.1 (3)
C13—C12—C11	115.5 (3)	C21—C22—H22	119.9
C13—C12—H12A	108.4	C17—C22—H22	119.9
C11—C12—H12A	108.4	O23—Cl2—O21	105.0 (2)
C13—C12—H12B	108.4	O23—Cl2—O22	110.1 (3)
C11—C12—H12B	108.4	O21—Cl2—O22	108.3 (2)
H12A—C12—H12B	107.5	O23—Cl2—O24	108.2 (2)
C14—C13—C12	115.8 (3)	O21—Cl2—O24	109.9 (2)
C14—C13—H13A	108.3	O22—Cl2—O24	115.0 (2)
C12—C13—H13A	108.3