#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/03/7150304.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_7150304
loop_
_publ_author_name
'Ley, Steven V.'
'Dixon, Darren J.'
'Guy, Richard T.'
'Rodríguez, Félix'
'Sheppard, Tom D.'
_publ_section_title
;
 Michael, Michael-aldol and Michael-Michael reactions of enolate
 equivalents of butane-2,3-diacetal protected glycolic acid
 derivatives.
;
_journal_issue                   22
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4095
_journal_page_last               4107
_journal_paper_doi               10.1039/b512410g
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C14 H22 O6'
_chemical_formula_sum            'C14 H22 O6'
_chemical_formula_weight         286.32
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5902(2)
_cell_length_b                   10.0809(2)
_cell_length_c                   16.5589(4)
_cell_measurement_reflns_used    6412
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.02
_cell_volume                     1433.95(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9517
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         4.21
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0357
_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)+(0.0297P)²+0.2875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0828
_reflns_number_gt                2959
_reflns_number_total             3278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b512410g.txt
_cod_data_source_block           sl0346
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7150304
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
O1 O 0.54934(13) -0.01424(12) 0.42060(7) 0.0436(3) Uani 1 1 d . . .
O2 O 0.87933(11) 0.01498(10) 0.28838(5) 0.0274(2) Uani 1 1 d . . .
O3 O 0.58829(12) -0.10650(11) 0.30253(6) 0.0327(2) Uani 1 1 d . . .
O4 O 0.68638(12) 0.09503(10) 0.20278(6) 0.0336(3) Uani 1 1 d . . .
O5 O 0.78726(12) -0.23667(10) 0.25037(6) 0.0334(2) Uani 1 1 d . . .
O6 O 1.21802(16) 0.17775(13) 0.52901(8) 0.0513(3) Uani 1 1 d . . .
C1 C 0.88743(16) 0.02442(13) 0.43285(8) 0.0246(3) Uani 1 1 d . . .
H1 H 0.8232 0.0475 0.4812 0.029 Uiso 1 1 calc R . .
C2 C 0.78733(16) 0.04762(13) 0.35767(8) 0.0260(3) Uani 1 1 d . . .
H2 H 0.7628 0.1445 0.3549 0.031 Uiso 1 1 calc R . .
C3 C 0.63427(16) -0.02708(15) 0.36342(9) 0.0295(3) Uani 1 1 d . . .
C4 C 0.68728(17) -0.13187(15) 0.23229(8) 0.0298(3) Uani 1 1 d . . .
C5 C 0.79158(16) -0.01007(15) 0.21739(8) 0.0289(3) Uani 1 1 d . . .
C6 C 0.90879(18) -0.03269(18) 0.15050(9) 0.0359(3) Uani 1 1 d . . .
H6A H 0.9711 0.0478 0.1428 0.054 Uiso 1 1 calc R . .
H6B H 0.8538 -0.0538 0.1003 0.054 Uiso 1 1 calc R . .
H6C H 0.9773 -0.1066 0.1651 0.054 Uiso 1 1 calc R . .
C7 C 0.57413(19) -0.16074(17) 0.16429(10) 0.0382(4) Uani 1 1 d . . .
H7A H 0.5008 -0.2297 0.1814 0.057 Uiso 1 1 calc R . .
H7B H 0.6318 -0.1915 0.1168 0.057 Uiso 1 1 calc R . .
H7C H 0.5167 -0.0798 0.1507 0.057 Uiso 1 1 calc R . .
C8 C 0.7574(2) 0.21924(18) 0.18255(12) 0.0449(4) Uani 1 1 d . . .
H8A H 0.6797 0.2902 0.1861 0.067 Uiso 1 1 calc R . .
H8B H 0.7985 0.2150 0.1274 0.067 Uiso 1 1 calc R . .
H8C H 0.8427 0.2375 0.2203 0.067 Uiso 1 1 calc R . .
C9 C 0.7150(2) -0.36446(16) 0.25876(11) 0.0410(4) Uani 1 1 d . . .
H9A H 0.7920 -0.4288 0.2781 0.062 Uiso 1 1 calc R . .
H9B H 0.6744 -0.3932 0.2063 0.062 Uiso 1 1 calc R . .
H9C H 0.6293 -0.3585 0.2976 0.062 Uiso 1 1 calc R . .
C10 C 1.02829(18) 0.11802(15) 0.43120(9) 0.0315(3) Uani 1 1 d . . .
H10A H 1.0770 0.1131 0.3771 0.038 Uiso 1 1 calc R . .
H10B H 0.9910 0.2101 0.4390 0.038 Uiso 1 1 calc R . .
C11 C 1.15061(18) 0.08903(16) 0.49386(9) 0.0328(3) Uani 1 1 d . . .
C12 C 1.18880(18) -0.05450(16) 0.50833(10) 0.0362(4) Uani 1 1 d . . .
H12A H 1.2486 -0.0625 0.5592 0.043 Uiso 1 1 calc R . .
H12B H 1.2555 -0.0872 0.4638 0.043 Uiso 1 1 calc R . .
C13 C 1.04317(19) -0.14109(16) 0.51380(10) 0.0342(3) Uani 1 1 d . . .
H13A H 0.9856 -0.1191 0.5638 0.041 Uiso 1 1 calc R . .
H13B H 1.0743 -0.2355 0.5168 0.041 Uiso 1 1 calc R . .
C14 C 0.93670(17) -0.12050(14) 0.44091(9) 0.0284(3) Uani 1 1 d . . .
H14A H 0.9919 -0.1484 0.3912 0.034 Uiso 1 1 calc R . .
H14B H 0.8429 -0.1768 0.4468 0.034 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C2 114.30(10) . . ?
C3 O3 C4 121.91(11) . . ?
C5 O4 C8 115.02(11) . . ?
C4 O5 C9 115.73(11) . . ?
C14 C1 C2 111.90(11) . . ?
C14 C1 C10 111.80(12) . . ?
C2 C1 C10 109.54(11) . . ?
C14 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
C10 C1 H1 107.8 . . ?
O2 C2 C3 114.49(11) . . ?
O2 C2 C1 107.85(10) . . ?
C3 C2 C1 111.08(11) . . ?
O2 C2 H2 107.7 . . ?
C3 C2 H2 107.7 . . ?
C1 C2 H2 107.7 . . ?
O1 C3 O3 118.40(13) . . ?
O1 C3 C2 121.44(13) . . ?
O3 C3 C2 120.12(12) . . ?
O5 C4 O3 108.65(11) . . ?
O5 C4 C7 114.15(13) . . ?
O3 C4 C7 104.56(11) . . ?
O5 C4 C5 106.27(11) . . ?
O3 C4 C5 109.03(12) . . ?
C7 C4 C5 114.03(12) . . ?
O4 C5 O2 110.37(12) . . ?
O4 C5 C6 114.38(11) . . ?
O2 C5 C6 106.23(11) . . ?
O4 C5 C4 104.66(11) . . ?
O2 C5 C4 108.56(11) . . ?
C6 C5 C4 112.58(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 114.75(12) . . ?
C11 C10 H10A 108.6 . . ?
C1 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C1 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
O6 C11 C12 121.92(15) . . ?
O6 C11 C10 121.36(15) . . ?
C12 C11 C10 116.69(13) . . ?
C11 C12 C13 112.38(13) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 111.44(12) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C1 C14 C13 111.39(12) . . ?
C1 C14 H14A 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C1 C14 H14B 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
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
O1 C3 1.2023(18) . ?
O2 C5 1.4190(15) . ?
O2 C2 1.4315(16) . ?
O3 C3 1.3468(18) . ?
O3 C4 1.4633(17) . ?
O4 C5 1.4134(17) . ?
O4 C8 1.4327(19) . ?
O5 C4 1.3940(18) . ?
O5 C9 1.4367(19) . ?
O6 C11 1.2141(18) . ?
C1 C14 1.5268(19) . ?
C1 C2 1.5310(19) . ?
C1 C10 1.5347(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.5182(19) . ?
C2 H2 1.0000 . ?
C4 C7 1.516(2) . ?
C4 C5 1.540(2) . ?
C5 C6 1.514(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.505(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.503(2) . ?
C12 C13 1.528(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
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
C5 O2 C2 C3 36.48(15) . . . . ?
C5 O2 C2 C1 160.66(11) . . . . ?
C14 C1 C2 O2 -61.81(14) . . . . ?
C10 C1 C2 O2 62.75(14) . . . . ?
C14 C1 C2 C3 64.40(15) . . . . ?
C10 C1 C2 C3 -171.04(11) . . . . ?
C4 O3 C3 O1 -177.45(13) . . . . ?
C4 O3 C3 C2 4.72(19) . . . . ?
O2 C2 C3 O1 176.20(13) . . . . ?
C1 C2 C3 O1 53.76(18) . . . . ?
O2 C2 C3 O3 -6.04(18) . . . . ?
C1 C2 C3 O3 -128.48(13) . . . . ?
C9 O5 C4 O3 68.70(15) . . . . ?
C9 O5 C4 C7 -47.54(17) . . . . ?
C9 O5 C4 C5 -174.10(12) . . . . ?
C3 O3 C4 O5 85.73(15) . . . . ?
C3 O3 C4 C7 -152.02(13) . . . . ?
C3 O3 C4 C5 -29.70(17) . . . . ?
C8 O4 C5 O2 66.76(16) . . . . ?
C8 O4 C5 C6 -52.95(18) . . . . ?
C8 O4 C5 C4 -176.62(13) . . . . ?
C2 O2 C5 O4 51.55(14) . . . . ?
C2 O2 C5 C6 176.07(11) . . . . ?
C2 O2 C5 C4 -62.62(15) . . . . ?
O5 C4 C5 O4 -177.54(10) . . . . ?
O3 C4 C5 O4 -60.59(13) . . . . ?
C7 C4 C5 O4 55.83(16) . . . . ?
O5 C4 C5 O2 -59.68(14) . . . . ?
O3 C4 C5 O2 57.27(14) . . . . ?
C7 C4 C5 O2 173.69(12) . . . . ?
O5 C4 C5 C6 57.64(15) . . . . ?
O3 C4 C5 C6 174.59(11) . . . . ?
C7 C4 C5 C6 -68.99(16) . . . . ?
C14 C1 C10 C11 -45.12(17) . . . . ?
C2 C1 C10 C11 -169.74(12) . . . . ?
C1 C10 C11 O6 -140.99(15) . . . . ?
C1 C10 C11 C12 41.17(19) . . . . ?
O6 C11 C12 C13 137.81(15) . . . . ?
C10 C11 C12 C13 -44.36(19) . . . . ?
C11 C12 C13 C14 52.30(18) . . . . ?
C2 C1 C14 C13 177.17(12) . . . . ?
C10 C1 C14 C13 53.87(16) . . . . ?
C12 C13 C14 C1 -58.09(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188865
