#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/77/1547714.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_1547714
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_formula_moiety         'C16 H20 O4'
_chemical_formula_sum            'C16 H20 O4'
_chemical_formula_weight         276.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 97.0200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.00500(10)
_cell_length_b                   11.0252(2)
_cell_length_c                   16.3524(3)
_cell_measurement_reflns_used    7083
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.23
_cell_volume                     1432.39(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11892
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0073(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   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.044
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0352P)²+0.4765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0865
_reflns_number_gt                2648
_reflns_number_total             3157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            41467_2017_787_MOESM6_ESM.cif
_cod_data_source_block           i13839
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1547714
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 1.33357(10) 0.63816(8) 0.25893(5) 0.0246(2) Uani 1 1 d . . .
O2 O 1.10566(9) 0.58079(7) 0.18090(5) 0.01752(19) Uani 1 1 d . . .
O3 O 0.87029(10) 0.86447(8) 0.08572(5) 0.0184(2) Uani 1 1 d . . .
O15 O 0.58825(11) 0.88004(9) 0.06774(6) 0.0297(2) Uani 1 1 d . . .
C1 C 1.21619(14) 0.66843(11) 0.20996(7) 0.0171(2) Uani 1 1 d . . .
C2 C 1.18513(14) 0.79738(11) 0.18211(7) 0.0168(2) Uani 1 1 d . . .
H2A H 1.1668 0.7993 0.1211 0.02 Uiso 1 1 calc R . .
H2B H 1.2868 0.8462 0.2002 0.02 Uiso 1 1 calc R . .
C3 C 1.03265(14) 0.85597(11) 0.21566(7) 0.0166(2) Uani 1 1 d . . .
H3 H 1.0412 0.9448 0.2046 0.02 Uiso 1 1 calc R . .
C4 C 0.86587(14) 0.81532(11) 0.16875(7) 0.0164(2) Uani 1 1 d . . .
H4 H 0.7723 0.8556 0.1937 0.02 Uiso 1 1 calc R . .
C5 C 0.82620(14) 0.67956(11) 0.15936(7) 0.0164(2) Uani 1 1 d . . .
H5 H 0.7224 0.6744 0.1187 0.02 Uiso 1 1 calc R . .
C6 C 0.96140(13) 0.60751(11) 0.12079(7) 0.0149(2) Uani 1 1 d . . .
H6 H 0.9994 0.6557 0.0747 0.018 Uiso 1 1 calc R . .
C7 C 1.04125(15) 0.84365(12) 0.30938(7) 0.0213(3) Uani 1 1 d . . .
H7A H 1.1373 0.8901 0.3359 0.032 Uiso 1 1 calc R . .
H7B H 1.0548 0.758 0.3248 0.032 Uiso 1 1 calc R . .
H7C H 0.9371 0.8749 0.3274 0.032 Uiso 1 1 calc R . .
C8 C 0.77962(16) 0.62062(12) 0.23801(8) 0.0250(3) Uani 1 1 d . . .
H8A H 0.6912 0.6683 0.2594 0.037 Uiso 1 1 calc R . .
H8B H 0.8791 0.6176 0.2793 0.037 Uiso 1 1 calc R . .
H8C H 0.7386 0.538 0.2258 0.037 Uiso 1 1 calc R . .
C9 C 0.89106(13) 0.48712(11) 0.08755(7) 0.0155(2) Uani 1 1 d . . .
C10 C 0.75944(14) 0.48880(11) 0.02293(7) 0.0181(3) Uani 1 1 d . . .
H10 H 0.7218 0.5641 -0.0009 0.022 Uiso 1 1 calc R . .
C11 C 0.68326(14) 0.38220(12) -0.00673(7) 0.0208(3) Uani 1 1 d . . .
H11 H 0.5928 0.3849 -0.0501 0.025 Uiso 1 1 calc R . .
C12 C 0.73847(15) 0.27138(12) 0.02661(7) 0.0214(3) Uani 1 1 d . . .
H12 H 0.6845 0.1983 0.0072 0.026 Uiso 1 1 calc R . .
C13 C 0.87301(15) 0.26834(11) 0.08845(7) 0.0204(3) Uani 1 1 d . . .
H13 H 0.9144 0.1926 0.1099 0.025 Uiso 1 1 calc R . .
C14 C 0.94818(14) 0.37567(11) 0.11940(7) 0.0176(2) Uani 1 1 d . . .
H14 H 1.039 0.3726 0.1625 0.021 Uiso 1 1 calc R . .
C15 C 0.72171(15) 0.89117(11) 0.04127(8) 0.0209(3) Uani 1 1 d . . .
C16 C 0.74666(17) 0.93321(13) -0.04331(8) 0.0267(3) Uani 1 1 d . . .
H16A H 0.8401 0.9912 -0.0397 0.04 Uiso 1 1 calc R . .
H16B H 0.6436 0.9726 -0.069 0.04 Uiso 1 1 calc R . .
H16C H 0.7726 0.8634 -0.0767 0.04 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
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 O2 C6 121.56(9) . .
C15 O3 C4 117.40(9) . .
O1 C1 O2 117.25(11) . .
O1 C1 C2 123.34(11) . .
O2 C1 C2 119.38(10) . .
C1 C2 C3 113.42(9) . .
C1 C2 H2A 108.9 . .
C3 C2 H2A 108.9 . .
C1 C2 H2B 108.9 . .
C3 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
C4 C3 C7 114.03(9) . .
C4 C3 C2 112.40(9) . .
C7 C3 C2 112.25(9) . .
C4 C3 H3 105.8 . .
C7 C3 H3 105.8 . .
C2 C3 H3 105.8 . .
O3 C4 C3 103.81(9) . .
O3 C4 C5 107.22(9) . .
C3 C4 C5 119.70(10) . .
O3 C4 H4 108.5 . .
C3 C4 H4 108.5 . .
C5 C4 H4 108.5 . .
C8 C5 C4 113.56(10) . .
C8 C5 C6 112.45(10) . .
C4 C5 C6 113.42(9) . .
C8 C5 H5 105.5 . .
C4 C5 H5 105.5 . .
C6 C5 H5 105.5 . .
O2 C6 C9 107.15(9) . .
O2 C6 C5 111.61(9) . .
C9 C6 C5 110.48(9) . .
O2 C6 H6 109.2 . .
C9 C6 H6 109.2 . .
C5 C6 H6 109.2 . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C5 C8 H8A 109.5 . .
C5 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C5 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C14 C9 C10 118.54(11) . .
C14 C9 C6 123.28(10) . .
C10 C9 C6 118.16(10) . .
C11 C10 C9 120.83(11) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C10 C11 C12 120.28(11) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C13 C12 C11 119.35(11) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C12 C13 C14 120.47(12) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C9 C14 C13 120.45(11) . .
C9 C14 H14 119.8 . .
C13 C14 H14 119.8 . .
O15 C15 O3 123.07(11) . .
O15 C15 C16 125.97(11) . .
O3 C15 C16 110.95(10) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2049(14) .
O2 C1 1.3562(14) .
O2 C6 1.4523(13) .
O3 C15 1.3485(14) .
O3 C4 1.4664(13) .
O15 C15 1.2069(15) .
C1 C2 1.5042(17) .
C2 C3 1.5401(15) .
C2 H2A 0.99 .
C2 H2B 0.99 .
C3 C4 1.5236(15) .
C3 C7 1.5317(15) .
C3 H3 1 .
C4 C5 1.5339(16) .
C4 H4 1 .
C5 C8 1.5273(16) .
C5 C6 1.5385(15) .
C5 H5 1 .
C6 C9 1.5164(16) .
C6 H6 1 .
C7 H7A 0.98 .
C7 H7B 0.98 .
C7 H7C 0.98 .
C8 H8A 0.98 .
C8 H8B 0.98 .
C8 H8C 0.98 .
C9 C14 1.3900(17) .
C9 C10 1.3982(15) .
C10 C11 1.3843(17) .
C10 H10 0.95 .
C11 C12 1.3879(18) .
C11 H11 0.95 .
C12 C13 1.3846(17) .
C12 H12 0.95 .
C13 C14 1.3943(17) .
C13 H13 0.95 .
C14 H14 0.95 .
C15 C16 1.4950(18) .
C16 H16A 0.98 .
C16 H16B 0.98 .
C16 H16C 0.98 .
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
C6 O2 C1 O1 -179.09(10) . . . .
C6 O2 C1 C2 2.59(14) . . . .
O1 C1 C2 C3 -108.93(13) . . . .
O2 C1 C2 C3 69.29(13) . . . .
C1 C2 C3 C4 -78.11(12) . . . .
C1 C2 C3 C7 52.01(13) . . . .
C15 O3 C4 C3 -151.58(10) . . . .
C15 O3 C4 C5 80.82(11) . . . .
C7 C3 C4 O3 165.53(9) . . . .
C2 C3 C4 O3 -65.26(11) . . . .
C7 C3 C4 C5 -75.06(13) . . . .
C2 C3 C4 C5 54.15(13) . . . .
O3 C4 C5 C8 -167.46(9) . . . .
C3 C4 C5 C8 74.88(13) . . . .
O3 C4 C5 C6 62.54(11) . . . .
C3 C4 C5 C6 -55.13(13) . . . .
C1 O2 C6 C9 166.78(9) . . . .
C1 O2 C6 C5 -72.16(12) . . . .
C8 C5 C6 O2 -50.97(12) . . . .
C4 C5 C6 O2 79.60(12) . . . .
C8 C5 C6 C9 68.14(12) . . . .
C4 C5 C6 C9 -161.29(9) . . . .
O2 C6 C9 C14 7.13(14) . . . .
C5 C6 C9 C14 -114.65(11) . . . .
O2 C6 C9 C10 -174.44(9) . . . .
C5 C6 C9 C10 63.78(13) . . . .
C14 C9 C10 C11 2.39(16) . . . .
C6 C9 C10 C11 -176.11(10) . . . .
C9 C10 C11 C12 -0.99(17) . . . .
C10 C11 C12 C13 -1.52(17) . . . .
C11 C12 C13 C14 2.60(16) . . . .
C10 C9 C14 C13 -1.31(16) . . . .
C6 C9 C14 C13 177.11(10) . . . .
C12 C13 C14 C9 -1.17(16) . . . .
C4 O3 C15 O15 2.43(17) . . . .
C4 O3 C15 C16 -176.65(10) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139051214
