#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:40:03 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178789 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/43/4104396.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_4104396
loop_
_publ_author_name
'Christopher J. Morten'
'Timothy F. Jamison'
_publ_section_title
;
 Water Overcomes Methyl Group Directing Effects in Epoxide-Opening
 Cascades
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6678
_journal_page_last               6679
_journal_paper_doi               10.1021/ja9025243
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H20 O4'
_chemical_formula_weight         228.28
_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                 112.4120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4928(3)
_cell_length_b                   5.17550(10)
_cell_length_c                   11.2885(3)
_cell_measurement_reflns_used    9709
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      4.24
_cell_volume                     566.72(3)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2008)'
_computing_data_collection       'APEX2 3.0 (Bruker-AXS, 2008)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0118
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10799
_diffrn_reflns_theta_full        67.66
_diffrn_reflns_theta_max         67.66
_diffrn_reflns_theta_min         4.24
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  0.9230
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(13)
_refine_ls_extinction_coef       0.0103(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2028
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0281
_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)+(0.0503P)²+0.0865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2005
_reflns_number_total             2028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9025243_si_002.cif
_cod_data_source_block           d09014
_cod_original_cell_volume        566.72(2)
_cod_database_code               4104396
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 0.36236(7) 0.46642(18) 0.76029(7) 0.0170(2) Uani 1 1 d .
O2 O 0.33137(7) 0.80928(15) 0.46470(7) 0.0151(2) Uani 1 1 d .
O3 O -0.00301(7) 0.47310(16) 0.34327(7) 0.0144(2) Uani 1 1 d .
O4 O -0.02720(8) 0.76477(19) 0.04092(7) 0.0179(2) Uani 1 1 d D
H4 H -0.0149(15) 0.911(3) 0.0209(14) 0.022 Uiso 1 1 d D
C1 C 0.50693(11) 0.5023(3) 0.83296(11) 0.0188(3) Uani 1 1 d .
H1A H 0.5596 0.3702 0.8071 0.023 Uiso 1 1 calc R
H1B H 0.5259 0.4773 0.9251 0.023 Uiso 1 1 calc R
C2 C 0.55583(11) 0.7711(3) 0.81308(11) 0.0194(3) Uani 1 1 d .
H2A H 0.6568 0.7844 0.8600 0.023 Uiso 1 1 calc R
H2B H 0.5113 0.9034 0.8477 0.023 Uiso 1 1 calc R
C3 C 0.51972(11) 0.8208(2) 0.67013(11) 0.0171(3) Uani 1 1 d .
H3A H 0.5433 1.0008 0.6568 0.021 Uiso 1 1 calc R
H3B H 0.5729 0.7026 0.6373 0.021 Uiso 1 1 calc R
C4 C 0.36640(11) 0.7752(2) 0.59939(11) 0.0151(3) Uani 1 1 d .
H4A H 0.3140 0.9033 0.6295 0.018 Uiso 1 1 calc R
C5 C 0.32843(11) 0.5011(2) 0.62626(10) 0.0143(3) Uani 1 1 d .
H5 H 0.3810 0.3730 0.5964 0.017 Uiso 1 1 calc R
C6 C 0.17449(11) 0.4540(3) 0.55541(10) 0.0149(3) Uani 1 1 d .
H6A H 0.1509 0.2742 0.5690 0.018 Uiso 1 1 calc R
H6B H 0.1207 0.5731 0.5871 0.018 Uiso 1 1 calc R
C7 C 0.14201(11) 0.5017(2) 0.41443(10) 0.0132(3) Uani 1 1 d .
H7 H 0.1926 0.3722 0.3830 0.016 Uiso 1 1 calc R
C8 C 0.18702(10) 0.7744(2) 0.39372(11) 0.0143(3) Uani 1 1 d .
H8 H 0.1346 0.9042 0.4229 0.017 Uiso 1 1 calc R
C9 C 0.15609(12) 0.8150(2) 0.25273(11) 0.0153(3) Uani 1 1 d .
H9A H 0.2131 0.6966 0.2245 0.018 Uiso 1 1 calc R
H9B H 0.1788 0.9947 0.2380 0.018 Uiso 1 1 calc R
C10 C 0.00319(11) 0.7624(2) 0.17572(10) 0.0149(3) Uani 1 1 d .
H10 H -0.0534 0.8974 0.1964 0.018 Uiso 1 1 calc R
C11 C -0.03810(11) 0.4944(2) 0.20777(10) 0.0142(3) Uani 1 1 d .
H11 H 0.0135 0.3596 0.1807 0.017 Uiso 1 1 calc R
C12 C -0.19136(11) 0.4438(3) 0.14120(10) 0.0188(3) Uani 1 1 d .
H12A H -0.2138 0.2764 0.1689 0.028 Uiso 1 1 calc R
H12B H -0.2164 0.4418 0.0482 0.028 Uiso 1 1 calc R
H12C H -0.2429 0.5806 0.1634 0.028 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C5 O1 C1 111.82(8)
C8 O2 C4 111.57(8)
C7 O3 C11 112.09(8)
C10 O4 H4 107.9(10)
O1 C1 C2 112.01(9)
O1 C1 H1A 109.2
C2 C1 H1A 109.2
O1 C1 H1B 109.2
C2 C1 H1B 109.2
H1A C1 H1B 107.9
C1 C2 C3 110.20(10)
C1 C2 H2A 109.6
C3 C2 H2A 109.6
C1 C2 H2B 109.6
C3 C2 H2B 109.6
H2A C2 H2B 108.1
C4 C3 C2 108.36(9)
C4 C3 H3A 110.0
C2 C3 H3A 110.0
C4 C3 H3B 110.0
C2 C3 H3B 110.0
H3A C3 H3B 108.4
O2 C4 C3 109.33(9)
O2 C4 C5 110.05(9)
C3 C4 C5 110.05(10)
O2 C4 H4A 109.1
C3 C4 H4A 109.1
C5 C4 H4A 109.1
O1 C5 C6 108.80(8)
O1 C5 C4 110.31(9)
C6 C5 C4 110.31(9)
O1 C5 H5 109.1
C6 C5 H5 109.1
C4 C5 H5 109.1
C7 C6 C5 107.10(9)
C7 C6 H6A 110.3
C5 C6 H6A 110.3
C7 C6 H6B 110.3
C5 C6 H6B 110.3
H6A C6 H6B 108.5
O3 C7 C6 109.74(8)
O3 C7 C8 109.42(9)
C6 C7 C8 110.53(9)
O3 C7 H7 109.0
C6 C7 H7 109.0
C8 C7 H7 109.0
O2 C8 C9 109.18(8)
O2 C8 C7 110.66(9)
C9 C8 C7 109.46(9)
O2 C8 H8 109.2
C9 C8 H8 109.2
C7 C8 H8 109.2
C8 C9 C10 109.33(9)
C8 C9 H9A 109.8
C10 C9 H9A 109.8
C8 C9 H9B 109.8
C10 C9 H9B 109.8
H9A C9 H9B 108.3
O4 C10 C9 111.29(9)
O4 C10 C11 106.83(9)
C9 C10 C11 110.82(9)
O4 C10 H10 109.3
C9 C10 H10 109.3
C11 C10 H10 109.3
O3 C11 C12 107.92(8)
O3 C11 C10 109.85(9)
C12 C11 C10 112.35(9)
O3 C11 H11 108.9
C12 C11 H11 108.9
C10 C11 H11 108.9
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.4274(12)
O1 C1 1.4351(13)
O2 C8 1.4295(12)
O2 C4 1.4325(13)
O3 C7 1.4320(12)
O3 C11 1.4345(12)
O4 C10 1.4308(13)
O4 H4 0.814(13)
C1 C2 1.5284(17)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.5322(16)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5172(14)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.5346(16)
C4 H4A 1.0000
C5 C6 1.5241(14)
C5 H5 1.0000
C6 C7 1.5154(14)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5342(15)
C7 H7 1.0000
C8 C9 1.5128(15)
C8 H8 1.0000
C9 C10 1.5298(14)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5367(16)
C10 H10 1.0000
C11 C12 1.5159(15)
C11 H11 1.0000
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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
O4 H4 O4 0.814(13) 2.066(13) 2.8772(7) 174.0(14) 2
