#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/67/1516752.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_1516752
loop_
_publ_author_name
'Hong, Bor-Cherng'
'Wu, Ming-Fun'
'Tseng, Hsing-Chang'
'Liao, Ju-Hsiou'
_publ_section_title
;
 Enantioselective organocatalytic formal [3 + 3]-cycloaddition of
 alpha,beta-unsaturated aldehydes and application to the asymmetric
 synthesis of (-)-isopulegol hydrate and (-)-cubebaol.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2217
_journal_page_last               2220
_journal_paper_doi               10.1021/ol060486+
_journal_volume                  8
_journal_year                    2006
_chemical_formula_sum            'C8 H12 O2'
_chemical_formula_weight         140.18
_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                 103.792(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.773(2)
_cell_length_b                   6.401(2)
_cell_length_c                   8.075(3)
_cell_measurement_temperature    298(2)
_cell_volume                     390.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3456
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9866
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1746
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0518
_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)+(0.0737P)²+0.0167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1583
_reflns_number_total             1746
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060486%2Bsi20060226_113516.cif
_cod_data_source_block           mfw410
_cod_original_cell_volume        390.1(2)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1516752
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 0.43067(18) 0.1288(3) 0.9925(2) 0.0677(5) Uani 1 1 d .
O2 O 0.2182(2) -0.2260(2) 0.8146(2) 0.0586(4) Uani 1 1 d .
C1 C 0.1405(2) 0.1419(3) 0.8149(2) 0.0405(4) Uani 1 1 d .
C2 C 0.0237(3) 0.2759(3) 0.7247(2) 0.0464(4) Uani 1 1 d .
H2 H 0.0636 0.4081 0.7039 0.056 Uiso 1 1 calc R
C3 C -0.1680(2) 0.2257(4) 0.6549(3) 0.0513(5) Uani 1 1 d .
H3A H -0.1900 0.2077 0.5323 0.062 Uiso 1 1 calc R
H3B H -0.2393 0.3423 0.6765 0.062 Uiso 1 1 calc R
C4 C -0.2252(2) 0.0288(4) 0.7331(2) 0.0462(5) Uani 1 1 d .
H4 H -0.2346 0.0619 0.8491 0.055 Uiso 1 1 calc R
C5 C -0.0860(3) -0.1406(3) 0.7440(2) 0.0466(4) Uani 1 1 d .
H5A H -0.1254 -0.2656 0.7922 0.056 Uiso 1 1 calc R
H5B H -0.0754 -0.1743 0.6298 0.056 Uiso 1 1 calc R
C6 C 0.0947(2) -0.0786(3) 0.8514(2) 0.0426(4) Uani 1 1 d .
H6 H 0.0937 -0.0900 0.9722 0.051 Uiso 1 1 calc R
C7 C 0.3181(3) 0.2224(4) 0.8902(3) 0.0512(5) Uani 1 1 d .
H7 H 0.3464 0.3547 0.8570 0.061 Uiso 1 1 calc R
C8 C -0.4055(3) -0.0459(4) 0.6316(3) 0.0638(6) Uani 1 1 d .
H8A H -0.3994 -0.0766 0.5167 0.096 Uiso 1 1 calc R
H8B H -0.4920 0.0614 0.6305 0.096 Uiso 1 1 calc R
H8C H -0.4387 -0.1697 0.6835 0.096 Uiso 1 1 calc R
H11 H 0.312(4) -0.200(6) 0.882(4) 0.083(9) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0412(8) 0.0633(10) 0.0851(10) -0.0074(9) -0.0117(7) 0.0035(8)
O2 0.0388(7) 0.0451(8) 0.0830(10) -0.0080(8) -0.0034(7) 0.0053(6)
C1 0.0347(9) 0.0411(10) 0.0445(8) -0.0046(7) 0.0070(7) -0.0013(8)
C2 0.0419(9) 0.0404(9) 0.0545(10) 0.0024(8) 0.0068(8) -0.0031(8)
C3 0.0392(9) 0.0501(12) 0.0591(10) 0.0019(9) 0.0009(8) 0.0046(9)
C4 0.0324(9) 0.0559(12) 0.0491(9) -0.0038(8) 0.0071(7) -0.0020(8)
C5 0.0376(9) 0.0432(11) 0.0571(10) -0.0009(8) 0.0072(8) -0.0052(8)
C6 0.0363(9) 0.0422(10) 0.0458(8) 0.0010(8) 0.0028(7) -0.0008(8)
C7 0.0381(10) 0.0455(12) 0.0673(11) -0.0083(9) 0.0070(9) -0.0039(9)
C8 0.0335(10) 0.0736(16) 0.0787(14) -0.0008(12) 0.0025(10) -0.0071(10)
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 C7 116.90(18)
C2 C1 C6 123.35(16)
C7 C1 C6 119.62(17)
C1 C2 C3 123.7(2)
C2 C3 C4 112.60(17)
C5 C4 C8 111.01(18)
C5 C4 C3 109.95(15)
C8 C4 C3 111.03(18)
C6 C5 C4 113.33(17)
O2 C6 C1 112.20(15)
O2 C6 C5 106.60(15)
C1 C6 C5 111.38(15)
O1 C7 C1 124.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.209(3)
O2 C6 1.426(2)
C1 C2 1.333(3)
C1 C7 1.463(2)
C1 C6 1.502(3)
C2 C3 1.497(3)
C3 C4 1.523(3)
C4 C5 1.519(3)
C4 C8 1.522(3)
C5 C6 1.517(3)
