#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/77/1547716.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_1547716
loop_
_publ_author_name
'Guo-Ming Ho'
'Medel Manuel L. Zulueta'
'Shang-Cheng Hung'
_publ_section_title
;
 Stereoselective one-pot synthesis of polypropionates
;
_journal_name_full               'Nature Cummunications'
_journal_page_first              679
_journal_paper_doi               10.1038/s41467-017-00787-y
_journal_volume                  8
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_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
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.574
_cell_length_b                   8.8
_cell_length_c                   17.704
_cell_measurement_reflns_used    8625
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      2.58
_cell_volume                     1335.788
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36941
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.03
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(7)
_refine_ls_extinction_coef       0.0044(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.2479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                2617
_reflns_number_total             2722
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            41467_2017_787_MOESM8_ESM.cif
_cod_data_source_block           i13165
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        1335.8
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1547716
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 0.88847(10) 0.59815(9) 0.25462(4) 0.01773(19) Uani 1 1 d . . .
O2 O 1.03705(11) 0.63244(11) 0.35647(5) 0.0250(2) Uani 1 1 d . . .
O3 O 0.48622(9) 0.44495(10) 0.14318(5) 0.01827(19) Uani 1 1 d . . .
O4 O 0.37027(11) 0.21635(10) 0.13689(5) 0.0245(2) Uani 1 1 d . . .
C1 C 0.94102(14) 0.55732(15) 0.32390(7) 0.0186(3) Uani 1 1 d . . .
C2 C 0.86216(16) 0.41233(15) 0.34870(7) 0.0234(3) Uani 1 1 d . . .
C3 C 0.78393(16) 0.35450(15) 0.27699(7) 0.0201(3) Uani 1 1 d . . .
C4 C 0.75918(14) 0.50076(14) 0.23202(7) 0.0170(3) Uani 1 1 d . . .
C5 C 0.76176(14) 0.48764(13) 0.14625(7) 0.0166(2) Uani 1 1 d . . .
C6 C 0.63447(14) 0.37749(14) 0.11937(7) 0.0172(2) Uani 1 1 d . . .
C7 C 0.63317(17) 0.35138(16) 0.03494(7) 0.0231(3) Uani 1 1 d . . .
C8 C 0.36339(14) 0.35101(14) 0.14945(7) 0.0192(2) Uani 1 1 d . . .
C9 C 0.22083(16) 0.43498(17) 0.17452(8) 0.0252(3) Uani 1 1 d . . .
C10 C 0.75393(14) 0.64147(13) 0.10750(6) 0.0173(2) Uani 1 1 d . . .
C11 C 0.84305(15) 0.66809(15) 0.04312(7) 0.0205(3) Uani 1 1 d . . .
C12 C 0.83755(17) 0.80711(16) 0.00589(8) 0.0249(3) Uani 1 1 d . . .
C13 C 0.74347(17) 0.92176(15) 0.03322(7) 0.0252(3) Uani 1 1 d . . .
C14 C 0.65340(16) 0.89834(15) 0.09714(7) 0.0240(3) Uani 1 1 d . . .
C15 C 0.65888(15) 0.75847(14) 0.13384(7) 0.0207(3) Uani 1 1 d . . .
H2B H 0.7870(19) 0.4416(18) 0.3873(9) 0.027(4) Uiso 1 1 d . . .
H2A H 0.9361(19) 0.345(2) 0.3718(9) 0.030(4) Uiso 1 1 d . . .
H3A H 0.853(2) 0.2897(19) 0.2508(9) 0.030(4) Uiso 1 1 d . . .
H3B H 0.6856(18) 0.3015(18) 0.2871(9) 0.024(4) Uiso 1 1 d . . .
H4 H 0.6663(16) 0.5502(15) 0.2481(7) 0.012(3) Uiso 1 1 d . . .
H5 H 0.8569(17) 0.4379(16) 0.1328(7) 0.016(3) Uiso 1 1 d . . .
H7A H 0.5576(19) 0.2715(18) 0.0197(9) 0.026(4) Uiso 1 1 d . . .
H7C H 0.608(2) 0.446(2) 0.0078(9) 0.034(4) Uiso 1 1 d . . .
H6 H 0.6499(16) 0.2795(16) 0.1440(7) 0.013(3) Uiso 1 1 d . . .
H7B H 0.740(2) 0.3163(19) 0.0182(9) 0.034(4) Uiso 1 1 d . . .
H9A H 0.208(2) 0.529(2) 0.1452(12) 0.055(6) Uiso 1 1 d . . .
H9B H 0.232(2) 0.464(2) 0.2259(12) 0.051(5) Uiso 1 1 d . . .
H9C H 0.133(2) 0.372(3) 0.1698(11) 0.055(6) Uiso 1 1 d . . .
H11 H 0.9131(16) 0.5868(17) 0.0247(8) 0.018(3) Uiso 1 1 d . . .
H12 H 0.896(2) 0.8258(19) -0.0394(10) 0.033(4) Uiso 1 1 d . . .
H13 H 0.7459(19) 1.0175(18) 0.0099(8) 0.023(4) Uiso 1 1 d . . .
H14 H 0.591(2) 0.979(2) 0.1162(9) 0.037(5) Uiso 1 1 d . . .
H15 H 0.5911(17) 0.7445(17) 0.1788(8) 0.021(4) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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
C1 O1 C4 110.21(9) . .
C8 O3 C6 117.04(9) . .
O2 C1 O1 121.04(12) . .
O2 C1 C2 129.18(11) . .
O1 C1 C2 109.78(10) . .
C1 C2 C3 103.73(10) . .
C1 C2 H2B 106.1(9) . .
C3 C2 H2B 112.5(9) . .
C1 C2 H2A 110.5(10) . .
C3 C2 H2A 116.1(10) . .
H2B C2 H2A 107.5(13) . .
C2 C3 C4 102.35(10) . .
C2 C3 H3A 109.6(10) . .
C4 C3 H3A 109.9(10) . .
C2 C3 H3B 112.7(9) . .
C4 C3 H3B 112.1(9) . .
H3A C3 H3B 109.9(13) . .
O1 C4 C5 107.90(9) . .
O1 C4 C3 104.28(9) . .
C5 C4 C3 116.97(10) . .
O1 C4 H4 106.6(8) . .
C5 C4 H4 110.2(8) . .
C3 C4 H4 110.2(8) . .
C10 C5 C4 112.46(10) . .
C10 C5 C6 113.03(9) . .
C4 C5 C6 110.27(9) . .
C10 C5 H5 109.5(8) . .
C4 C5 H5 107.2(8) . .
C6 C5 H5 103.9(8) . .
O3 C6 C7 109.85(10) . .
O3 C6 C5 105.77(9) . .
C7 C6 C5 114.05(10) . .
O3 C6 H6 110.3(8) . .
C7 C6 H6 108.0(8) . .
C5 C6 H6 108.9(8) . .
C6 C7 H7A 112.4(9) . .
C6 C7 H7C 110.7(9) . .
H7A C7 H7C 108.9(13) . .
C6 C7 H7B 109.2(9) . .
H7A C7 H7B 107.2(12) . .
H7C C7 H7B 108.3(14) . .
O4 C8 O3 123.40(12) . .
O4 C8 C9 125.43(12) . .
O3 C8 C9 111.17(10) . .
C8 C9 H9A 110.7(12) . .
C8 C9 H9B 109.7(12) . .
H9A C9 H9B 107.0(17) . .
C8 C9 H9C 109.7(13) . .
H9A C9 H9C 110.9(17) . .
H9B C9 H9C 108.8(17) . .
C11 C10 C15 118.08(11) . .
C11 C10 C5 119.70(11) . .
C15 C10 C5 122.22(10) . .
C12 C11 C10 121.17(12) . .
C12 C11 H11 120.0(8) . .
C10 C11 H11 118.8(8) . .
C13 C12 C11 119.81(12) . .
C13 C12 H12 118.2(10) . .
C11 C12 H12 122.0(10) . .
C12 C13 C14 120.24(12) . .
C12 C13 H13 119.3(9) . .
C14 C13 H13 120.4(9) . .
C13 C14 C15 119.59(12) . .
C13 C14 H14 119.4(10) . .
C15 C14 H14 120.9(10) . .
C14 C15 C10 121.11(12) . .
C14 C15 H15 117.6(9) . .
C10 C15 H15 121.2(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3552(14) .
O1 C4 1.4572(14) .
O2 C1 1.2031(15) .
O3 C8 1.3435(14) .
O3 C6 1.4648(14) .
O4 C8 1.2071(16) .
C1 C2 1.5093(18) .
C2 C3 1.5234(17) .
C2 H2B 0.974(16) .
C2 H2A 0.959(17) .
C3 C4 1.5282(17) .
C3 H3A 0.943(17) .
C3 H3B 0.980(16) .
C4 C5 1.5231(16) .
C4 H4 0.951(14) .
C5 C10 1.5191(16) .
C5 C6 1.5352(17) .
C5 H5 0.956(15) .
C6 C7 1.5124(16) .
C6 H6 0.976(14) .
C7 H7A 0.994(16) .
C7 H7C 0.988(17) .
C7 H7B 1.014(18) .
C8 C9 1.4956(18) .
C9 H9A 0.98(2) .
C9 H9B 0.95(2) .
C9 H9C 0.94(2) .
C10 C11 1.3920(17) .
C10 C15 1.3935(17) .
C11 C12 1.3903(19) .
C11 H11 0.989(14) .
C12 C13 1.379(2) .
C12 H12 0.959(17) .
C13 C14 1.385(2) .
C13 H13 0.939(16) .
C14 C15 1.3925(18) .
C14 H14 0.952(18) .
C15 H15 0.994(15) .
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
C4 O1 C1 O2 -172.54(11) . . . .
C4 O1 C1 C2 7.70(13) . . . .
O2 C1 C2 C3 -167.23(13) . . . .
O1 C1 C2 C3 12.51(14) . . . .
C1 C2 C3 C4 -26.11(13) . . . .
C1 O1 C4 C5 -149.74(10) . . . .
C1 O1 C4 C3 -24.71(12) . . . .
C2 C3 C4 O1 30.81(12) . . . .
C2 C3 C4 C5 149.85(10) . . . .
O1 C4 C5 C10 -56.62(12) . . . .
C3 C4 C5 C10 -173.69(10) . . . .
O1 C4 C5 C6 176.22(9) . . . .
C3 C4 C5 C6 59.14(14) . . . .
C8 O3 C6 C7 78.16(13) . . . .
C8 O3 C6 C5 -158.33(10) . . . .
C10 C5 C6 O3 -64.88(12) . . . .
C4 C5 C6 O3 61.96(12) . . . .
C10 C5 C6 C7 55.94(14) . . . .
C4 C5 C6 C7 -177.22(10) . . . .
C6 O3 C8 O4 0.34(17) . . . .
C6 O3 C8 C9 179.67(10) . . . .
C4 C5 C10 C11 140.82(11) . . . .
C6 C5 C10 C11 -93.50(13) . . . .
C4 C5 C10 C15 -39.66(15) . . . .
C6 C5 C10 C15 86.01(13) . . . .
C15 C10 C11 C12 -0.12(18) . . . .
C5 C10 C11 C12 179.41(11) . . . .
C10 C11 C12 C13 0.6(2) . . . .
C11 C12 C13 C14 -0.6(2) . . . .
C12 C13 C14 C15 0.2(2) . . . .
C13 C14 C15 C10 0.21(19) . . . .
C11 C10 C15 C14 -0.26(18) . . . .
C5 C10 C15 C14 -179.79(11) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139051216
