
data_publication_text


data_miesch1636
#TrackingRef '03 tw lm mm cyclobutanone.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 O4'
_chemical_formula_sum            'C19 H24 O4'
_chemical_formula_weight         316.38
_chemical_absolute_configuration rm

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2220(10)
_cell_length_b                   10.0520(14)
_cell_length_c                   9.8200(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.015(9)
_cell_angle_gamma                90.00
_cell_volume                     879.23(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1972
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      29.131

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4268
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         29.13
_reflns_number_total             2486
_reflns_number_gt                1499
_reflns_threshold_expression     I>2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
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 > 2sigma(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         2486
_refine_ls_number_parameters     210
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1039
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0554(3) 0.1186(2) -0.5555(3) 0.0341(6) Uani 1 1 d . . .
H1 H -0.0550 0.1047 -0.5704 0.041 Uiso 1 1 calc R . .
C2 C 0.0891(3) 0.1887(3) -0.6851(3) 0.0412(7) Uani 1 1 d . . .
H2 H 0.1645 0.2622 -0.6607 0.049 Uiso 1 1 calc R . .
C3 C -0.0473(3) 0.2209(3) -0.8062(3) 0.0501(8) Uani 1 1 d . . .
H3A H -0.1261 0.2657 -0.7710 0.060 Uiso 1 1 calc R . .
H3B H -0.0190 0.2792 -0.8765 0.060 Uiso 1 1 calc R . .
C4 C -0.1014(3) 0.0859(3) -0.8701(3) 0.0472(8) Uani 1 1 d . . .
H4A H -0.1636 0.0956 -0.9682 0.057 Uiso 1 1 calc R . .
H4B H -0.1608 0.0396 -0.8138 0.057 Uiso 1 1 calc R . .
C5 C 0.0432(3) 0.0105(3) -0.8659(3) 0.0518(8) Uani 1 1 d . . .
H5A H 0.0819 0.0339 -0.9479 0.062 Uiso 1 1 calc R . .
H5B H 0.0266 -0.0868 -0.8659 0.062 Uiso 1 1 calc R . .
C6 C 0.1526(3) 0.0553(3) -0.7278(3) 0.0433(7) Uani 1 1 d . . .
H6 H 0.2599 0.0599 -0.7313 0.052 Uiso 1 1 calc R . .
C7 C 0.1294(3) -0.0058(3) -0.5950(3) 0.0362(6) Uani 1 1 d . . .
C8 C 0.1247(3) 0.1756(3) -0.4104(3) 0.0348(6) Uani 1 1 d . . .
H8 H 0.0844 0.2670 -0.4037 0.042 Uiso 1 1 calc R . .
C9 C 0.3525(3) 0.3027(3) -0.3727(3) 0.0490(8) Uani 1 1 d . . .
C10 C 0.5197(3) 0.2880(4) -0.3366(4) 0.0729(11) Uani 1 1 d . . .
H10A H 0.5649 0.3717 -0.3563 0.109 Uiso 1 1 calc R . .
H10B H 0.5465 0.2165 -0.3934 0.109 Uiso 1 1 calc R . .
H10C H 0.5572 0.2662 -0.2363 0.109 Uiso 1 1 calc R . .
C11 C 0.1025(3) 0.0907(3) -0.2889(3) 0.0387(7) Uani 1 1 d . . .
H11 H 0.1495 0.0014 -0.2913 0.046 Uiso 1 1 calc R . .
C12 C -0.0613(3) 0.0743(3) -0.2926(3) 0.0476(8) Uani 1 1 d . . .
H12A H -0.0699 0.0276 -0.2075 0.071 Uiso 1 1 calc R . .
H12B H -0.1118 0.0227 -0.3761 0.071 Uiso 1 1 calc R . .
H12C H -0.1085 0.1621 -0.2967 0.071 Uiso 1 1 calc R . .
C13 C 0.3096(3) 0.0986(3) -0.0820(3) 0.0439(7) Uani 1 1 d . . .
H13A H 0.3801 0.0895 -0.1423 0.053 Uiso 1 1 calc R . .
H13B H 0.2890 0.0087 -0.0504 0.053 Uiso 1 1 calc R . .
C14 C 0.3790(3) 0.1841(3) 0.0440(3) 0.0378(7) Uani 1 1 d . . .
C15 C 0.3256(3) 0.3097(3) 0.0600(3) 0.0487(8) Uani 1 1 d . . .
H15 H 0.2429 0.3443 -0.0099 0.058 Uiso 1 1 calc R . .
C16 C 0.3915(3) 0.3860(3) 0.1771(3) 0.0532(8) Uani 1 1 d . . .
H16 H 0.3540 0.4725 0.1868 0.064 Uiso 1 1 calc R . .
C17 C 0.5104(4) 0.3374(3) 0.2788(4) 0.0556(9) Uani 1 1 d . . .
H17 H 0.5555 0.3901 0.3589 0.067 Uiso 1 1 calc R . .
C18 C 0.5644(3) 0.2121(4) 0.2648(3) 0.0562(9) Uani 1 1 d . . .
H18 H 0.6469 0.1780 0.3352 0.067 Uiso 1 1 calc R . .
C19 C 0.4987(3) 0.1359(3) 0.1484(3) 0.0482(8) Uani 1 1 d . . .
H19 H 0.5361 0.0491 0.1397 0.058 Uiso 1 1 calc R . .
O1 O 0.1626(2) -0.11194(19) -0.5381(2) 0.0470(5) Uani 1 1 d . . .
O2 O 0.28681(19) 0.18253(18) -0.39341(19) 0.0405(5) Uani 1 1 d . . .
O3 O 0.2857(3) 0.4058(2) -0.3803(3) 0.0719(8) Uani 1 1 d . . .
O4 O 0.17443(19) 0.15763(18) -0.15991(18) 0.0436(5) Uani 1 1 d . . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.516(3) . ?
C1 C7 1.522(4) . ?
C1 C2 1.555(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.524(4) . ?
C2 C6 1.564(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.525(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.534(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.505(4) . ?
C6 H6 1.0000 . ?
C7 O1 1.207(3) . ?
C8 O2 1.462(3) . ?
C8 C11 1.522(4) . ?
C8 H8 1.0000 . ?
C9 O3 1.198(4) . ?
C9 O2 1.343(4) . ?
C9 C10 1.497(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O4 1.436(3) . ?
C11 C12 1.511(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O4 1.413(3) . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.379(4) . ?
C14 C19 1.385(4) . ?
C15 C16 1.384(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.368(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C7 116.3(2) . . ?
C8 C1 C2 118.3(2) . . ?
C7 C1 C2 88.1(2) . . ?
C8 C1 H1 110.8 . . ?
C7 C1 H1 110.8 . . ?
C2 C1 H1 110.8 . . ?
C3 C2 C1 115.8(2) . . ?
C3 C2 C6 105.3(2) . . ?
C1 C2 C6 89.9(2) . . ?
C3 C2 H2 114.3 . . ?
C1 C2 H2 114.3 . . ?
C6 C2 H2 114.3 . . ?
C4 C3 C2 104.4(2) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C3 C4 C5 103.9(2) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
C4 C5 C6 104.4(2) . . ?
C4 C5 H5A 110.9 . . ?
C6 C5 H5A 110.9 . . ?
C4 C5 H5B 110.9 . . ?
C6 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C7 C6 C5 115.9(2) . . ?
C7 C6 C2 88.3(2) . . ?
C5 C6 C2 106.4(2) . . ?
C7 C6 H6 114.4 . . ?
C5 C6 H6 114.4 . . ?
C2 C6 H6 114.4 . . ?
O1 C7 C6 133.3(3) . . ?
O1 C7 C1 133.2(3) . . ?
C6 C7 C1 93.4(2) . . ?
O2 C8 C1 107.1(2) . . ?
O2 C8 C11 106.18(19) . . ?
C1 C8 C11 114.6(2) . . ?
O2 C8 H8 109.6 . . ?
C1 C8 H8 109.6 . . ?
C11 C8 H8 109.6 . . ?
O3 C9 O2 124.3(3) . . ?
O3 C9 C10 125.6(3) . . ?
O2 C9 C10 110.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 C12 107.6(2) . . ?
O4 C11 C8 107.7(2) . . ?
C12 C11 C8 112.3(2) . . ?
O4 C11 H11 109.7 . . ?
C12 C11 H11 109.7 . . ?
C8 C11 H11 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 C14 109.4(2) . . ?
O4 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
O4 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C13 121.9(2) . . ?
C19 C14 C13 119.7(3) . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C9 O2 C8 117.9(2) . . ?
C13 O4 C11 114.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C3 -129.9(2) . . . . ?
C7 C1 C2 C3 111.1(2) . . . . ?
C8 C1 C2 C6 123.1(2) . . . . ?
C7 C1 C2 C6 4.12(19) . . . . ?
C1 C2 C3 C4 -70.7(3) . . . . ?
C6 C2 C3 C4 26.8(3) . . . . ?
C2 C3 C4 C5 -39.6(3) . . . . ?
C3 C4 C5 C6 36.5(3) . . . . ?
C4 C5 C6 C7 76.6(3) . . . . ?
C4 C5 C6 C2 -19.7(3) . . . . ?
C3 C2 C6 C7 -121.0(2) . . . . ?
C1 C2 C6 C7 -4.2(2) . . . . ?
C3 C2 C6 C5 -4.4(3) . . . . ?
C1 C2 C6 C5 112.4(2) . . . . ?
C5 C6 C7 O1 79.4(4) . . . . ?
C2 C6 C7 O1 -173.1(3) . . . . ?
C5 C6 C7 C1 -103.2(3) . . . . ?
C2 C6 C7 C1 4.3(2) . . . . ?
C8 C1 C7 O1 52.3(4) . . . . ?
C2 C1 C7 O1 173.1(3) . . . . ?
C8 C1 C7 C6 -125.1(2) . . . . ?
C2 C1 C7 C6 -4.3(2) . . . . ?
C7 C1 C8 O2 47.9(3) . . . . ?
C2 C1 C8 O2 -55.0(3) . . . . ?
C7 C1 C8 C11 -69.6(3) . . . . ?
C2 C1 C8 C11 -172.5(2) . . . . ?
O2 C8 C11 O4 61.8(3) . . . . ?
C1 C8 C11 O4 179.85(19) . . . . ?
O2 C8 C11 C12 -179.9(2) . . . . ?
C1 C8 C11 C12 -61.9(3) . . . . ?
O4 C13 C14 C15 -9.9(4) . . . . ?
O4 C13 C14 C19 169.4(3) . . . . ?
C19 C14 C15 C16 0.7(4) . . . . ?
C13 C14 C15 C16 179.9(3) . . . . ?
C14 C15 C16 C17 -0.2(5) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C14 0.5(5) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C13 C14 C19 C18 179.9(3) . . . . ?
O3 C9 O2 C8 -7.3(4) . . . . ?
C10 C9 O2 C8 171.6(2) . . . . ?
C1 C8 O2 C9 118.9(3) . . . . ?
C11 C8 O2 C9 -118.2(3) . . . . ?
C14 C13 O4 C11 175.6(2) . . . . ?
C12 C11 O4 C13 131.8(2) . . . . ?
C8 C11 O4 C13 -107.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.038


