#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:46:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178443 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/64/4026402.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_4026402
loop_
_publ_author_name
'Christopher P. Hencken'
'Douglas T. Genna'
'Maxime A. Siegler'
'Gary H. Posner'
_publ_contact_author_address
;Department of Chemistry
Johns Hopkins University
Baltimore
MD 21218
USA
;
_publ_contact_author_email       ghp@jhu.edu
_publ_contact_author_name        'Gary H. Posner'
_publ_contact_author_phone       '(410) 516-4670'
_publ_section_title
;
 Highly Stereocontrolled and Regiocontrolled Syntheses of
 2,3,4-Trisubstituted Alkanoates and Lactones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5149
_journal_page_last               5155
_journal_paper_doi               10.1021/jo200795f
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.931(4)
_cell_angle_beta                 84.067(3)
_cell_angle_gamma                88.465(3)
_cell_formula_units_Z            2
_cell_length_a                   5.9601(3)
_cell_length_b                   9.2461(4)
_cell_length_c                   12.9839(5)
_cell_measurement_reflns_used    3679
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      1.60
_cell_volume                     698.42(5)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
;
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 15.9890
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Goniometer KM4/Xcalibur, detector: Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7374
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug  2 2010,13:00:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       needle
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2445
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0395
_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)+(0.0368P)²+0.2022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                1845
_reflns_number_total             2445
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo200795f_si_002_4.cif
_cod_data_source_block           9
_cod_database_code               4026402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.53944(18) 0.23819(12) 0.17638(9) 0.0177(3) Uani 1 1 d .
O2 O 0.32934(19) 0.23812(13) 0.04034(9) 0.0216(3) Uani 1 1 d .
O3 O 0.23042(19) 0.53726(12) 0.03415(9) 0.0200(3) Uani 1 1 d .
O4 O -0.20667(19) 0.65682(13) 0.16731(11) 0.0223(3) Uani 1 1 d .
H4A H -0.202(4) 0.681(2) 0.099(2) 0.050(7) Uiso 1 1 d .
C1 C 0.4012(3) 0.29777(18) 0.10525(13) 0.0164(4) Uani 1 1 d .
C2 C 0.3369(3) 0.45068(18) 0.11993(13) 0.0164(4) Uani 1 1 d .
H2 H 0.4401 0.5026 0.1567 0.020 Uiso 1 1 calc R
C3 C 0.0944(3) 0.48683(18) 0.13220(13) 0.0166(4) Uani 1 1 d .
H3 H -0.0105 0.4041 0.1325 0.020 Uiso 1 1 calc R
C4 C 0.0075(3) 0.59916(18) 0.19552(13) 0.0174(4) Uani 1 1 d .
H4 H 0.1181 0.6814 0.1851 0.021 Uiso 1 1 calc R
C5 C -0.0243(3) 0.52657(18) 0.31180(14) 0.0204(4) Uani 1 1 d .
H5A H -0.1398 0.4489 0.3213 0.024 Uiso 1 1 calc R
H5B H 0.1192 0.4779 0.3316 0.024 Uiso 1 1 calc R
C6 C -0.0944(3) 0.62986(18) 0.38622(13) 0.0187(4) Uani 1 1 d .
C7 C 0.0634(3) 0.71898(18) 0.41503(13) 0.0197(4) Uani 1 1 d .
H7 H 0.2153 0.7181 0.3846 0.024 Uiso 1 1 calc R
C8 C 0.0026(3) 0.80873(19) 0.48712(14) 0.0226(4) Uani 1 1 d .
H8 H 0.1128 0.8686 0.5060 0.027 Uiso 1 1 calc R
C9 C -0.2179(3) 0.81193(19) 0.53204(14) 0.0229(4) Uani 1 1 d .
H9 H -0.2594 0.8726 0.5823 0.028 Uiso 1 1 calc R
C10 C -0.3769(3) 0.7259(2) 0.50291(15) 0.0263(4) Uani 1 1 d .
H10 H -0.5288 0.7277 0.5331 0.032 Uiso 1 1 calc R
C11 C -0.3165(3) 0.63690(19) 0.42995(14) 0.0226(4) Uani 1 1 d .
H11 H -0.4283 0.5799 0.4095 0.027 Uiso 1 1 calc R
C12 C 0.6290(3) 0.08476(18) 0.18055(13) 0.0182(4) Uani 1 1 d .
C13 C 0.7741(3) 0.0663(2) 0.27174(15) 0.0264(4) Uani 1 1 d .
H13A H 0.8434 -0.0321 0.2818 0.040 Uiso 1 1 calc R
H13B H 0.6800 0.0779 0.3362 0.040 Uiso 1 1 calc R
H13C H 0.8925 0.1411 0.2561 0.040 Uiso 1 1 calc R
C14 C 0.4360(3) -0.02444(19) 0.20575(14) 0.0235(4) Uani 1 1 d .
H14A H 0.3404 -0.0085 0.1475 0.035 Uiso 1 1 calc R
H14B H 0.3461 -0.0102 0.2707 0.035 Uiso 1 1 calc R
H14C H 0.4969 -0.1251 0.2154 0.035 Uiso 1 1 calc R
C15 C 0.7700(3) 0.07531(19) 0.07827(14) 0.0238(4) Uani 1 1 d .
H15A H 0.6730 0.0901 0.0206 0.036 Uiso 1 1 calc R
H15B H 0.8423 -0.0220 0.0841 0.036 Uiso 1 1 calc R
H15C H 0.8860 0.1517 0.0638 0.036 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
C1 O1 C12 121.17(12)
C2 O3 C3 61.69(10)
C4 O4 H4A 109.4(15)
O2 C1 O1 126.33(16)
O2 C1 C2 123.94(15)
O1 C1 C2 109.68(13)
O3 C2 C3 59.31(10)
O3 C2 C1 114.43(13)
C3 C2 C1 117.48(14)
O3 C2 H2 117.5
C3 C2 H2 117.5
C1 C2 H2 117.5
O3 C3 C2 59.00(10)
O3 C3 C4 117.97(13)
C2 C3 C4 121.00(14)
O3 C3 H3 115.7
C2 C3 H3 115.7
C4 C3 H3 115.7
O4 C4 C3 111.85(13)
O4 C4 C5 107.11(14)
C3 C4 C5 109.07(14)
O4 C4 H4 109.6
C3 C4 H4 109.6
C5 C4 H4 109.6
C6 C5 C4 114.92(14)
C6 C5 H5A 108.5
C4 C5 H5A 108.5
C6 C5 H5B 108.5
C4 C5 H5B 108.5
H5A C5 H5B 107.5
C11 C6 C7 117.98(15)
C11 C6 C5 121.31(15)
C7 C6 C5 120.69(15)
C8 C7 C6 121.04(16)
C8 C7 H7 119.5
C6 C7 H7 119.5
C7 C8 C9 120.37(16)
C7 C8 H8 119.8
C9 C8 H8 119.8
C10 C9 C8 119.21(16)
C10 C9 H9 120.4
C8 C9 H9 120.4
C9 C10 C11 120.45(17)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C6 120.92(16)
C10 C11 H11 119.5
C6 C11 H11 119.5
O1 C12 C15 109.63(13)
O1 C12 C13 102.18(13)
C15 C12 C13 111.17(14)
O1 C12 C14 110.01(13)
C15 C12 C14 112.92(14)
C13 C12 C14 110.41(15)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.332(2)
O1 C12 1.4955(19)
O2 C1 1.2097(19)
O3 C2 1.436(2)
O3 C3 1.4403(19)
O4 C4 1.426(2)
O4 H4A 0.87(2)
C1 C2 1.497(2)
C2 C3 1.475(2)
C2 H2 1.0000
C3 C4 1.495(2)
C3 H3 1.0000
C4 C5 1.525(2)
C4 H4 1.0000
C5 C6 1.507(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C11 1.390(2)
C6 C7 1.391(2)
C7 C8 1.381(2)
C7 H7 0.9500
C8 C9 1.384(2)
C8 H8 0.9500
C9 C10 1.380(3)
C9 H9 0.9500
C10 C11 1.385(2)
C10 H10 0.9500
C11 H11 0.9500
C12 C15 1.512(2)
C12 C13 1.518(2)
C12 C14 1.519(2)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 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 H4A O2 0.87(2) 2.03(3) 2.8481(18) 155(2) 2_565
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
C12 O1 C1 O2 1.9(2)
C12 O1 C1 C2 179.47(13)
C3 O3 C2 C1 108.65(15)
O2 C1 C2 O3 -15.7(2)
O1 C1 C2 O3 166.75(13)
O2 C1 C2 C3 51.0(2)
O1 C1 C2 C3 -126.55(15)
C2 O3 C3 C4 111.18(16)
C1 C2 C3 O3 -103.49(15)
O3 C2 C3 C4 -106.09(16)
C1 C2 C3 C4 150.42(15)
O3 C3 C4 O4 89.72(17)
C2 C3 C4 O4 158.54(14)
O3 C3 C4 C5 -151.99(13)
C2 C3 C4 C5 -83.16(19)
O4 C4 C5 C6 -63.32(18)
C3 C4 C5 C6 175.46(14)
C4 C5 C6 C11 102.35(19)
C4 C5 C6 C7 -79.1(2)
C11 C6 C7 C8 1.8(3)
C5 C6 C7 C8 -176.85(16)
C6 C7 C8 C9 -0.2(3)
C7 C8 C9 C10 -0.8(3)
C8 C9 C10 C11 0.3(3)
C9 C10 C11 C6 1.4(3)
C7 C6 C11 C10 -2.3(3)
C5 C6 C11 C10 176.27(16)
C1 O1 C12 C15 62.15(18)
C1 O1 C12 C13 -179.87(14)
C1 O1 C12 C14 -62.59(19)
