gem-Chloro­nitro­socyclo­do­decane, (CH₂)_n-1CNOCl, with n = 12

The title compound, C₁₂H₂₂ClNO, adopts the square conform­ation [3333] observed in other known saturated twelve-membered rings. Disorder is observed, resulting from exchange of the chloro and nitroso substituents.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.054
• wR factor = 0.155
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?
PLAT241_ALERT_2_A Check High   U(eq) as Compared to Neighbors  for         N1
PLAT241_ALERT_2_A Check High   U(eq) as Compared to Neighbors  for         N2
PLAT242_ALERT_2_A Check Low    U(eq) as Compared to Neighbors  for         C1

Alert level B
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        Cl1
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors  for        Cl2

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.821     0.960
            Tmin' and Tmax expected:      0.921     0.960
            RR' =      0.892
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.89
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT215_ALERT_3_C Disordered N2      has ADP max/min Ratio .......       3.80
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors  for         O1
PLAT301_ALERT_3_C Main Residue  Disorder .........................      17.00 Perc.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  O1      ..       2.69 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3B    ..  O2      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4A    ..  O2      ..       2.91 Ang.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      15.00 Deg.
              N2   -C1   -CL1     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      12.80 Deg.
              N1   -C1   -CL2     1.555   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.10

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.05
           From the CIF: _reflns_number_total               3072
           Count of symmetry unique reflns         1833
           Completeness (_total/calc)            167.59%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1239
           Fraction of Friedel pairs measured     0.676
           Are heavy atom types Z>Si present          yes

   4 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  12 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
   9 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
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

1,1-chloronitroso-cyclododecane

Crystal data

C12H22ClNO	Dx = 1.177 Mg m^−3
Mr = 231.76	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 600 reflections
a = 8.3801 (19) Å	θ = 2.5–28.1°
b = 9.543 (2) Å	µ = 0.27 mm^−1
c = 16.348 (4) Å	T = 293 K
V = 1307.4 (5) Å^3	Cubic, blue
Z = 4	0.3 × 0.2 × 0.15 mm
F(000) = 504

Data collection

Bruker SMART APEX diffractometer	3072 independent reflections
Radiation source: fine-focus sealed tube	1998 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 0.3 pixels mm^-1	θmax = 28.1°, θmin = 2.5°
φ–ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→11
Tmin = 0.821, Tmax = 0.960	l = −21→21
11518 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0985P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
3072 reflections	Δρmax = 0.29 e Å^−3
163 parameters	Δρmin = −0.25 e Å^−3
40 restraints	Absolute structure: Flack (1983), 1239 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (10)

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 an 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	Occ. (<1)
Cl1	0.0234 (3)	0.1355 (2)	0.10869 (13)	0.0858 (5)	0.5
N1	0.1232 (16)	0.4093 (12)	0.0929 (7)	0.160 (7)	0.5
O1	0.0208 (11)	0.4134 (8)	0.0489 (5)	0.140 (3)	0.5
Cl2	0.0912 (4)	0.4096 (3)	0.07133 (18)	0.0882 (5)	0.5
N2	0.0811 (9)	0.1337 (10)	0.1099 (8)	0.201 (8)	0.5
O2	−0.0359 (9)	0.1385 (7)	0.0774 (5)	0.128 (2)	0.5
C1	0.1491 (2)	0.2729 (2)	0.13722 (12)	0.0620 (5)
C2	0.3202 (2)	0.2327 (2)	0.12095 (13)	0.0697 (6)
H2A	0.3469	0.154	0.1559	0.084*
H2B	0.3282	0.2009	0.0648	0.084*
C3	0.4424 (3)	0.3456 (3)	0.13416 (14)	0.0748 (6)
H3A	0.4092	0.4032	0.18	0.09*
H3B	0.4457	0.405	0.086	0.09*
C4	0.6101 (3)	0.2900 (3)	0.15092 (15)	0.0804 (7)
H4A	0.635	0.2178	0.1111	0.096*
H4B	0.6862	0.3655	0.1436	0.096*
C5	0.6295 (3)	0.2298 (3)	0.23611 (16)	0.0818 (7)
H5A	0.5415	0.1664	0.247	0.098*
H5B	0.7273	0.1755	0.238	0.098*
C6	0.6347 (3)	0.3399 (3)	0.30275 (16)	0.0841 (7)
H6A	0.5559	0.4113	0.2903	0.101*
H6B	0.7388	0.3845	0.3017	0.101*
C7	0.6040 (4)	0.2857 (3)	0.38898 (17)	0.0972 (8)
H7A	0.6209	0.3617	0.4274	0.117*
H7B	0.6814	0.2131	0.4012	0.117*
C8	0.4356 (3)	0.2260 (3)	0.40205 (15)	0.0906 (8)
H8A	0.4195	0.1502	0.3634	0.109*
H8B	0.4305	0.1861	0.4566	0.109*
C9	0.2998 (3)	0.3285 (3)	0.39282 (15)	0.0863 (7)
H9A	0.3253	0.3931	0.3489	0.104*
H9B	0.2905	0.3825	0.4429	0.104*
C10	0.1410 (3)	0.2609 (3)	0.37476 (14)	0.0868 (8)
H10A	0.0571	0.3295	0.383	0.104*
H10B	0.1236	0.1851	0.4133	0.104*
C11	0.1287 (3)	0.2029 (3)	0.28785 (14)	0.0765 (6)
H11B	0.2242	0.1496	0.2756	0.092*
H11C	0.0384	0.1395	0.2848	0.092*
C12	0.1087 (3)	0.3166 (3)	0.22430 (12)	0.0715 (6)
H12C	0.1761	0.3952	0.2392	0.086*
H12A	−0.001	0.3489	0.2256	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0621 (13)	0.1001 (11)	0.0953 (11)	−0.0167 (9)	−0.0169 (8)	−0.0097 (9)
N1	0.153 (8)	0.233 (12)	0.095 (7)	0.010 (7)	−0.065 (5)	0.035 (6)
O1	0.172 (7)	0.114 (4)	0.134 (5)	0.002 (5)	−0.047 (4)	0.029 (4)
Cl2	0.0991 (15)	0.0975 (11)	0.0682 (13)	0.0106 (10)	−0.0250 (12)	0.0215 (8)
N2	0.055 (4)	0.202 (10)	0.347 (16)	−0.039 (5)	−0.089 (6)	0.075 (10)
O2	0.126 (5)	0.118 (4)	0.141 (5)	−0.040 (4)	−0.018 (4)	−0.008 (4)
C1	0.0674 (12)	0.0579 (11)	0.0608 (11)	0.0011 (10)	−0.0058 (9)	0.0050 (9)
C2	0.0756 (13)	0.0745 (14)	0.0591 (11)	0.0032 (11)	0.0025 (9)	−0.0074 (10)
C3	0.0790 (14)	0.0735 (14)	0.0720 (12)	−0.0059 (11)	0.0048 (10)	0.0073 (10)
C4	0.0669 (13)	0.0892 (17)	0.0849 (14)	−0.0071 (12)	0.0129 (11)	−0.0059 (13)
C5	0.0698 (13)	0.0785 (15)	0.0970 (17)	0.0063 (12)	−0.0100 (12)	−0.0076 (13)
C6	0.0832 (15)	0.0766 (15)	0.0925 (16)	−0.0099 (14)	−0.0135 (13)	−0.0042 (13)
C7	0.113 (2)	0.0971 (19)	0.0813 (15)	−0.0090 (17)	−0.0363 (14)	0.0009 (14)
C8	0.118 (2)	0.0896 (18)	0.0639 (12)	−0.0041 (17)	−0.0146 (13)	0.0114 (12)
C9	0.1150 (19)	0.0819 (15)	0.0620 (12)	−0.0046 (15)	0.0011 (12)	−0.0116 (12)
C10	0.1085 (19)	0.0904 (17)	0.0613 (13)	−0.0043 (16)	0.0188 (12)	−0.0016 (11)
C11	0.0916 (15)	0.0695 (13)	0.0683 (12)	−0.0158 (12)	0.0014 (11)	0.0059 (10)
C12	0.0706 (12)	0.0773 (14)	0.0665 (12)	0.0031 (11)	0.0075 (10)	0.0006 (10)

Geometric parameters (Å, º)

Cl1—C1	1.746 (3)	C6—C7	1.524 (4)
N1—O1	1.121 (7)	C6—H6A	0.97
N1—C1	1.505 (9)	C6—H6B	0.97
Cl2—C1	1.760 (3)	C7—C8	1.537 (4)
N2—O2	1.116 (7)	C7—H7A	0.97
N2—C1	1.514 (8)	C7—H7B	0.97
C1—C2	1.507 (3)	C8—C9	1.507 (4)
C1—C12	1.522 (3)	C8—H8A	0.97
C2—C3	1.503 (3)	C8—H8B	0.97
C2—H2A	0.97	C9—C10	1.508 (4)
C2—H2B	0.97	C9—H9A	0.97
C3—C4	1.528 (3)	C9—H9B	0.97
C3—H3A	0.97	C10—C11	1.528 (3)
C3—H3B	0.97	C10—H10A	0.97
C4—C5	1.515 (4)	C10—H10B	0.97
C4—H4A	0.97	C11—C12	1.511 (3)
C4—H4B	0.97	C11—H11B	0.97
C5—C6	1.515 (4)	C11—H11C	0.97
C5—H5A	0.97	C12—H12C	0.97
C5—H5B	0.97	C12—H12A	0.97
O1—N1—C1	116.7 (10)	C5—C6—H6A	108.5
O2—N2—C1	115.8 (9)	C7—C6—H6A	108.5
N1—C1—C2	105.8 (6)	C5—C6—H6B	108.5
N1—C1—N2	124.2 (6)	C7—C6—H6B	108.5
C2—C1—N2	94.7 (4)	H6A—C6—H6B	107.5
N1—C1—C12	100.4 (5)	C6—C7—C8	114.2 (2)
C2—C1—C12	116.52 (18)	C6—C7—H7A	108.7
N2—C1—C12	115.7 (5)	C8—C7—H7A	108.7
N1—C1—Cl1	115.7 (4)	C6—C7—H7B	108.7
C2—C1—Cl1	109.59 (17)	C8—C7—H7B	108.7
N2—C1—Cl1	15.0 (3)	H7A—C7—H7B	107.6
C12—C1—Cl1	108.77 (17)	C9—C8—C7	116.0 (2)
N1—C1—Cl2	12.8 (4)	C9—C8—H8A	108.3
C2—C1—Cl2	110.05 (18)	C7—C8—H8A	108.3
N2—C1—Cl2	111.5 (4)	C9—C8—H8B	108.3
C12—C1—Cl2	107.93 (17)	C7—C8—H8B	108.3
Cl1—C1—Cl2	103.12 (16)	H8A—C8—H8B	107.4
C3—C2—C1	116.1 (2)	C8—C9—C10	114.1 (2)
C3—C2—H2A	108.3	C8—C9—H9A	108.7
C1—C2—H2A	108.3	C10—C9—H9A	108.7
C3—C2—H2B	108.3	C8—C9—H9B	108.7
C1—C2—H2B	108.3	C10—C9—H9B	108.7
H2A—C2—H2B	107.4	H9A—C9—H9B	107.6
C2—C3—C4	113.8 (2)	C9—C10—C11	113.3 (2)
C2—C3—H3A	108.8	C9—C10—H10A	108.9
C4—C3—H3A	108.8	C11—C10—H10A	108.9
C2—C3—H3B	108.8	C9—C10—H10B	108.9
C4—C3—H3B	108.8	C11—C10—H10B	108.9
H3A—C3—H3B	107.7	H10A—C10—H10B	107.7
C5—C4—C3	113.3 (2)	C12—C11—C10	112.7 (2)
C5—C4—H4A	108.9	C12—C11—H11B	109
C3—C4—H4A	108.9	C10—C11—H11B	109
C5—C4—H4B	108.9	C12—C11—H11C	109
C3—C4—H4B	108.9	C10—C11—H11C	109
H4A—C4—H4B	107.7	H11B—C11—H11C	107.8
C6—C5—C4	113.6 (2)	C11—C12—C1	114.9 (2)
C6—C5—H5A	108.8	C11—C12—H12C	108.5
C4—C5—H5A	108.8	C1—C12—H12C	108.5
C6—C5—H5B	108.8	C11—C12—H12A	108.5
C4—C5—H5B	108.8	C1—C12—H12A	108.5
H5A—C5—H5B	107.7	H12C—C12—H12A	107.5
C5—C6—C7	115.1 (2)
O1—N1—C1—C2	125.7 (13)	C1—C2—C3—C4	156.64 (19)
O1—N1—C1—N2	18.4 (18)	C2—C3—C4—C5	−74.4 (3)
O1—N1—C1—C12	−112.7 (13)	C3—C4—C5—C6	−73.1 (3)
O1—N1—C1—Cl1	4.2 (16)	C4—C5—C6—C7	162.5 (2)
O1—N1—C1—Cl2	14.5 (17)	C5—C6—C7—C8	−64.3 (3)
O2—N2—C1—N1	−31.3 (15)	C6—C7—C8—C9	−63.5 (3)
O2—N2—C1—C2	−144.0 (11)	C7—C8—C9—C10	158.4 (2)
O2—N2—C1—C12	93.5 (12)	C8—C9—C10—C11	−72.5 (3)
O2—N2—C1—Cl1	28.0 (11)	C9—C10—C11—C12	−74.4 (3)
O2—N2—C1—Cl2	−30.3 (13)	C10—C11—C12—C1	161.1 (2)
N1—C1—C2—C3	48.5 (5)	N1—C1—C12—C11	−177.7 (5)
N2—C1—C2—C3	176.1 (5)	C2—C1—C12—C11	−64.1 (3)
C12—C1—C2—C3	−62.1 (3)	N2—C1—C12—C11	45.9 (4)
Cl1—C1—C2—C3	173.90 (17)	Cl1—C1—C12—C11	60.4 (2)
Cl2—C1—C2—C3	61.2 (2)	Cl2—C1—C12—C11	171.57 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O1^i	0.97	2.69	3.533 (8)	145
C3—H3B···O2^i	0.97	2.71	3.467 (8)	135
C4—H4A···O2^ii	0.97	2.91	3.511 (8)	121

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