#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:09:45 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178887 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/16/4111681.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4111681
loop_
_publ_author_name
'Tarek Sammakia'
'Deidre M. Johns'
'Ganghyeok Kim'
'Martin A. Berliner'
_publ_section_title
;
 Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder
 Reaction: Application to the Total Synthesis of (+)-Dihydrocompactin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6504
_journal_page_last               6505
_journal_paper_doi               10.1021/ja043506g
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C16 H26 O3'
_chemical_formula_weight         266.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.83(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.521(3)
_cell_length_b                   7.874(4)
_cell_length_c                   18.048(8)
_cell_measurement_reflns_used    1607
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      29.885
_cell_measurement_theta_min      2.826
_cell_volume                     779.0(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  ' Siemens SMART CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0577
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7622
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.14
_diffrn_standards_decay_%        0(1)
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -4.1(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0512
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0727P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1304
_reflns_number_gt                1842
_reflns_number_total             2760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja043506gsi20041112_114411.cif
_cod_data_source_block           bc426
_cod_database_code               4111681
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1 O -0.0691(4) 0.9207(3) 0.11205(11) 0.0369(5) Uani 1 1 d .
O2 O -0.1314(3) 0.9330(3) 0.43482(9) 0.0293(5) Uani 1 1 d .
H2A H -0.1877 0.8469 0.4542 0.035 Uiso 1 1 calc R
O3 O -0.7907(3) 1.1644(3) 0.48080(11) 0.0383(5) Uani 1 1 d .
H3A H -0.8735 1.0821 0.4622 0.046 Uiso 1 1 calc R
C1 C 0.0979(5) 0.6686(4) 0.17339(14) 0.0254(6) Uani 1 1 d .
H1A H 0.2595 0.6606 0.2047 0.030 Uiso 1 1 calc R
C2 C 0.1018(5) 0.8222(4) 0.12285(15) 0.0286(7) Uani 1 1 d .
C3 C 0.3202(6) 0.8314(4) 0.08096(17) 0.0340(8) Uani 1 1 d .
H3B H 0.4703 0.8415 0.1166 0.041 Uiso 1 1 calc R
H3C H 0.3082 0.9329 0.0484 0.041 Uiso 1 1 calc R
C4 C 0.3337(6) 0.6707(5) 0.03336(16) 0.0404(8) Uani 1 1 d .
H4A H 0.2050 0.6760 -0.0097 0.048 Uiso 1 1 calc R
H4B H 0.4935 0.6675 0.0137 0.048 Uiso 1 1 calc R
C5 C 0.3021(6) 0.5081(5) 0.07697(16) 0.0366(8) Uani 1 1 d .
H5A H 0.4483 0.4898 0.1135 0.044 Uiso 1 1 calc R
H5B H 0.2869 0.4104 0.0422 0.044 Uiso 1 1 calc R
C6 C 0.0748(5) 0.5172(4) 0.11833(15) 0.0287(7) Uani 1 1 d .
H6A H -0.0681 0.5406 0.0803 0.034 Uiso 1 1 calc R
C7 C 0.0235(6) 0.3548(4) 0.15685(17) 0.0371(8) Uani 1 1 d .
H7A H 0.0466 0.2503 0.1323 0.045 Uiso 1 1 calc R
C8 C -0.0531(6) 0.3510(5) 0.22398(18) 0.0407(8) Uani 1 1 d .
H8A H -0.0825 0.2423 0.2439 0.049 Uiso 1 1 calc R
C9 C -0.0971(6) 0.5007(4) 0.27071(16) 0.0334(7) Uani 1 1 d .
H9A H -0.2630 0.4862 0.2868 0.040 Uiso 1 1 calc R
C10 C -0.1022(5) 0.6679(4) 0.22514(14) 0.0257(6) Uani 1 1 d .
H10A H -0.2619 0.6712 0.1926 0.031 Uiso 1 1 calc R
C11 C 0.0867(6) 0.4975(5) 0.34189(17) 0.0463(9) Uani 1 1 d .
H11A H 0.0771 0.3877 0.3670 0.056 Uiso 1 1 calc R
H11B H 0.0479 0.5887 0.3755 0.056 Uiso 1 1 calc R
H11C H 0.2521 0.5140 0.3285 0.056 Uiso 1 1 calc R
C12 C -0.0914(5) 0.8270(4) 0.27532(16) 0.0298(7) Uani 1 1 d .
H12A H 0.0510 0.8176 0.3140 0.036 Uiso 1 1 calc R
H12B H -0.0670 0.9284 0.2446 0.036 Uiso 1 1 calc R
C13 C -0.3224(5) 0.8519(4) 0.31364(16) 0.0321(7) Uani 1 1 d .
H13A H -0.4594 0.8804 0.2752 0.039 Uiso 1 1 calc R
H13B H -0.3624 0.7431 0.3368 0.039 Uiso 1 1 calc R
C14 C -0.3018(5) 0.9900(4) 0.37328(15) 0.0270(7) Uani 1 1 d .
H14A H -0.2392 1.0966 0.3522 0.032 Uiso 1 1 calc R
C15 C -0.5487(5) 1.0240(4) 0.39858(15) 0.0289(7) Uani 1 1 d .
H15A H -0.6133 0.9159 0.4162 0.035 Uiso 1 1 calc R
H15B H -0.6613 1.0622 0.3550 0.035 Uiso 1 1 calc R
C16 C -0.5496(5) 1.1548(5) 0.45986(15) 0.0315(7) Uani 1 1 d .
H16A H -0.4330 1.1217 0.5034 0.038 Uiso 1 1 calc R
H16B H -0.5000 1.2669 0.4419 0.038 Uiso 1 1 calc R
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 0.0016 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C10 115.7(3)
C2 C1 C6 103.5(2)
C10 C1 C6 112.3(2)
O1 C2 C3 122.8(3)
O1 C2 C1 122.5(3)
C3 C2 C1 114.3(3)
C2 C3 C4 109.7(3)
C5 C4 C3 112.8(2)
C4 C5 C6 111.2(3)
C7 C6 C5 113.3(3)
C7 C6 C1 111.4(2)
C5 C6 C1 109.8(2)
C8 C7 C6 122.6(3)
C7 C8 C9 126.2(3)
C8 C9 C11 108.9(3)
C8 C9 C10 111.5(2)
C11 C9 C10 115.2(3)
C1 C10 C12 112.1(2)
C1 C10 C9 111.0(3)
C12 C10 C9 112.4(2)
C13 C12 C10 113.1(2)
C14 C13 C12 114.4(2)
O2 C14 C15 110.6(2)
O2 C14 C13 108.0(2)
C15 C14 C13 110.2(2)
C14 C15 C16 115.0(2)
O3 C16 C15 108.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.219(4)
O2 C14 1.439(3)
O3 C16 1.428(3)
C1 C2 1.517(4)
C1 C10 1.529(4)
C1 C6 1.547(4)
C2 C3 1.499(4)
C3 C4 1.536(5)
C4 C5 1.523(5)
C5 C6 1.536(4)
C6 C7 1.499(4)
C7 C8 1.330(4)
C8 C9 1.486(5)
C9 C11 1.540(4)
C9 C10 1.551(4)
C10 C12 1.543(4)
C12 C13 1.534(4)
C13 C14 1.525(4)
C14 C15 1.512(4)
C15 C16 1.512(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.84 1.87 2.671(3) 159.7 2_446
O3 H3A O2 0.84 1.87 2.679(3) 162.4 1_455
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
C10 C1 C2 O1 -14.9(4)
C6 C1 C2 O1 108.4(3)
C10 C1 C2 C3 171.7(2)
C6 C1 C2 C3 -65.1(3)
O1 C2 C3 C4 -115.4(3)
C1 C2 C3 C4 58.0(3)
C2 C3 C4 C5 -48.0(3)
C3 C4 C5 C6 50.5(3)
C4 C5 C6 C7 175.1(2)
C4 C5 C6 C1 -59.6(3)
C2 C1 C6 C7 -169.9(2)
C10 C1 C6 C7 -44.4(3)
C2 C1 C6 C5 63.7(3)
C10 C1 C6 C5 -170.8(2)
C5 C6 C7 C8 140.3(3)
C1 C6 C7 C8 15.9(4)
C6 C7 C8 C9 -0.6(5)
C7 C8 C9 C11 -114.7(4)
C7 C8 C9 C10 13.4(5)
C2 C1 C10 C12 -56.6(3)
C6 C1 C10 C12 -175.2(2)
C2 C1 C10 C9 176.8(2)
C6 C1 C10 C9 58.3(3)
C8 C9 C10 C1 -41.2(3)
C11 C9 C10 C1 83.6(3)
C8 C9 C10 C12 -167.6(3)
C11 C9 C10 C12 -42.8(3)
C1 C10 C12 C13 166.1(2)
C9 C10 C12 C13 -68.1(3)
C10 C12 C13 C14 170.4(2)
C12 C13 C14 O2 -68.2(3)
C12 C13 C14 C15 170.9(3)
O2 C14 C15 C16 58.6(3)
C13 C14 C15 C16 178.0(3)
C14 C15 C16 O3 -176.3(2)
