#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/39/1503973.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_1503973
loop_
_publ_author_name
'Majetich, George'
'Grove, Jeremy L.'
_publ_section_title
;
 Total synthesis of (+)-19-deoxyicetexone, (-)-icetexone, and
 (+)-5-epi-icetexone.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2904
_journal_page_last               2907
_journal_paper_doi               10.1021/ol9009128
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H22 O5'
_chemical_formula_weight         342.38
_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                   7.747(3)
_cell_length_b                   10.338(4)
_cell_length_c                   20.948(9)
_cell_measurement_reflns_used    3121
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.268
_cell_measurement_theta_min      2.750
_cell_volume                     1677.7(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'BRUKER APEX II'
_diffrn_measurement_method       OMEGA-SCAN
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21275
_diffrn_reflns_theta_full        31.87
_diffrn_reflns_theta_max         31.87
_diffrn_reflns_theta_min         2.77
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0462
_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)+(0.0613P)²+0.4003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1437
_reflns_number_gt                1930
_reflns_number_total             3233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9009128_si_003.cif
_cod_data_source_block           j5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1677.8(12)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1503973
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 1.1329(3) 0.7349(2) 0.06851(10) 0.0526(6) Uani 1 1 d .
O2 O 1.1113(3) 0.4965(2) 0.03188(10) 0.0534(6) Uani 1 1 d .
H2C H 1.0906 0.4225 0.0201 0.080 Uiso 1 1 calc R
O3 O 0.5072(3) 0.5451(2) 0.04419(10) 0.0523(5) Uani 1 1 d .
O4 O 0.8351(3) 0.79185(18) 0.21349(9) 0.0435(5) Uani 1 1 d .
O5 O 0.6967(4) 0.6812(2) 0.28887(11) 0.0692(7) Uani 1 1 d .
C1 C 0.9170(5) 1.0174(3) 0.21661(14) 0.0561(8) Uani 1 1 d .
H1A H 0.8897 1.1029 0.2004 0.067 Uiso 1 1 calc R
H1B H 1.0388 1.0017 0.2094 0.067 Uiso 1 1 calc R
C2 C 0.8791(6) 1.0120(4) 0.28803(16) 0.0722(11) Uani 1 1 d .
H2A H 0.9204 1.0908 0.3079 0.087 Uiso 1 1 calc R
H2B H 0.9418 0.9401 0.3067 0.087 Uiso 1 1 calc R
C3 C 0.6879(6) 0.9962(4) 0.30234(16) 0.0694(11) Uani 1 1 d .
H3A H 0.6745 0.9699 0.3465 0.083 Uiso 1 1 calc R
H3B H 0.6315 1.0794 0.2973 0.083 Uiso 1 1 calc R
C4 C 0.5976(5) 0.8974(3) 0.25951(14) 0.0492(7) Uani 1 1 d .
C5 C 0.6190(4) 0.9423(3) 0.18943(13) 0.0418(6) Uani 1 1 d .
H5A H 0.5982 1.0357 0.1871 0.050 Uiso 1 1 calc R
C6 C 0.4980(4) 0.8750(3) 0.14482(14) 0.0449(7) Uani 1 1 d .
H6A H 0.3849 0.9046 0.1473 0.054 Uiso 1 1 calc R
C7 C 0.5210(4) 0.7812(3) 0.10232(13) 0.0426(6) Uani 1 1 d .
H7A H 0.4210 0.7531 0.0820 0.051 Uiso 1 1 calc R
C8 C 0.6774(3) 0.7158(3) 0.08276(11) 0.0346(5) Uani 1 1 d .
C9 C 0.8365(3) 0.7679(3) 0.08671(11) 0.0342(5) Uani 1 1 d .
C10 C 0.8112(4) 0.9170(3) 0.18098(12) 0.0389(6) Uani 1 1 d .
C11 C 0.9850(4) 0.6922(3) 0.06674(11) 0.0372(6) Uani 1 1 d .
C12 C 0.9618(4) 0.5580(3) 0.04513(12) 0.0392(6) Uani 1 1 d .
C13 C 0.8049(4) 0.5036(3) 0.03884(12) 0.0405(6) Uani 1 1 d .
C14 C 0.6537(4) 0.5837(3) 0.05411(11) 0.0364(6) Uani 1 1 d .
C15 C 0.7756(5) 0.3654(3) 0.01719(15) 0.0513(8) Uani 1 1 d .
H15A H 0.6507 0.3503 0.0177 0.062 Uiso 1 1 calc R
C16 C 0.8366(6) 0.3444(4) -0.05109(16) 0.0731(11) Uani 1 1 d .
H16A H 0.7823 0.4066 -0.0786 0.110 Uiso 1 1 calc R
H16B H 0.8063 0.2587 -0.0646 0.110 Uiso 1 1 calc R
H16C H 0.9596 0.3548 -0.0531 0.110 Uiso 1 1 calc R
C17 C 0.8561(6) 0.2689(3) 0.06241(18) 0.0717(11) Uani 1 1 d .
H17A H 0.8149 0.2845 0.1049 0.108 Uiso 1 1 calc R
H17B H 0.9794 0.2780 0.0615 0.108 Uiso 1 1 calc R
H17C H 0.8252 0.1828 0.0495 0.108 Uiso 1 1 calc R
C18 C 0.4151(5) 0.8720(4) 0.28209(18) 0.0703(11) Uani 1 1 d .
H18A H 0.4174 0.8438 0.3257 0.105 Uiso 1 1 calc R
H18B H 0.3636 0.8061 0.2560 0.105 Uiso 1 1 calc R
H18C H 0.3487 0.9501 0.2788 0.105 Uiso 1 1 calc R
C19 C 0.7077(4) 0.7769(3) 0.25747(13) 0.0467(7) Uani 1 1 d .
C20 C 0.8697(4) 0.9005(3) 0.11203(13) 0.0412(6) Uani 1 1 d .
H20A H 0.8099 0.9630 0.0855 0.049 Uiso 1 1 calc R
H20B H 0.9924 0.9187 0.1093 0.049 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 0.0000 '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 0.0000 '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
C19 O4 C10 108.8(2)
C10 C1 C2 110.7(3)
C1 C2 C3 112.6(3)
C4 C3 C2 113.7(3)
C19 C4 C18 113.2(3)
C19 C4 C3 108.0(3)
C18 C4 C3 111.1(3)
C19 C4 C5 99.2(2)
C18 C4 C5 116.6(3)
C3 C4 C5 107.9(3)
C6 C5 C10 117.4(2)
C6 C5 C4 112.7(2)
C10 C5 C4 99.4(2)
C7 C6 C5 132.4(3)
C6 C7 C8 130.0(3)
C9 C8 C7 124.2(3)
C9 C8 C14 120.0(2)
C7 C8 C14 115.8(2)
C8 C9 C11 119.4(2)
C8 C9 C20 123.2(3)
C11 C9 C20 117.4(2)
O4 C10 C1 107.8(2)
O4 C10 C20 107.6(2)
C1 C10 C20 112.4(2)
O4 C10 C5 102.7(2)
C1 C10 C5 110.7(2)
C20 C10 C5 114.9(2)
O1 C11 C9 122.4(3)
O1 C11 C12 117.5(3)
C9 C11 C12 120.0(2)
O2 C12 C13 123.9(3)
O2 C12 C11 113.7(2)
C13 C12 C11 122.3(3)
C12 C13 C14 117.6(2)
C12 C13 C15 123.9(3)
C14 C13 C15 118.5(3)
O3 C14 C13 121.3(2)
O3 C14 C8 118.6(3)
C13 C14 C8 120.1(2)
C13 C15 C16 111.7(3)
C13 C15 C17 111.9(3)
C16 C15 C17 111.5(3)
O5 C19 O4 121.4(3)
O5 C19 C4 129.0(3)
O4 C19 C4 109.6(2)
C9 C20 C10 112.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.229(3)
O2 C12 1.350(4)
O3 C14 1.221(3)
O4 C19 1.359(4)
O4 C10 1.474(3)
O5 C19 1.191(3)
C1 C10 1.519(4)
C1 C2 1.526(5)
C2 C3 1.520(6)
C3 C4 1.529(5)
C4 C19 1.510(5)
C4 C18 1.513(5)
C4 C5 1.549(4)
C5 C6 1.495(4)
C5 C10 1.522(4)
C6 C7 1.329(4)
C7 C8 1.446(4)
C8 C9 1.347(4)
C8 C14 1.503(4)
C9 C11 1.453(4)
C9 C20 1.493(4)
C10 C20 1.524(4)
C11 C12 1.471(4)
C12 C13 1.346(4)
C13 C14 1.470(4)
C13 C15 1.516(4)
C15 C16 1.522(5)
C15 C17 1.511(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 14313637
