#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/75/1507574.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_1507574
loop_
_publ_author_name
'Zhang, Qiang'
'Porco, Jr, John A'
_publ_section_title
;
 Total Synthesis of (+-)-7-epi-Nemorosone.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1796
_journal_page_last               1799
_journal_paper_doi               10.1021/ol300386t
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C26 H28 O5'
_chemical_formula_sum            'C26 H28 O5'
_chemical_formula_weight         420.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.029(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5279(4)
_cell_length_b                   12.1776(7)
_cell_length_c                   21.2420(12)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      33.38
_cell_measurement_theta_min      2.92
_cell_volume                     2202.9(2)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT+'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20656
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_correction_T_min  0.9497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.966
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0676P)²+1.0399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                4719
_reflns_number_total             5449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol300386t_si_002.cif
_cod_data_source_block           porco231
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1507574
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
O1 O 0.13357(11) 0.40929(8) 0.04982(4) 0.0251(2) Uani 1 1 d .
O2 O 0.19352(12) 0.26433(8) 0.23326(5) 0.0284(2) Uani 1 1 d .
O3 O 0.39987(11) 0.48076(8) 0.17390(5) 0.0278(2) Uani 1 1 d .
O4 O 0.33740(12) 0.65691(9) 0.19366(5) 0.0324(2) Uani 1 1 d .
O5 O -0.09557(12) 0.21201(9) 0.11257(5) 0.0346(2) Uani 1 1 d .
C1 C 0.12567(13) 0.44204(10) 0.10319(6) 0.0195(2) Uani 1 1 d .
C2 C 0.16552(15) 0.56093(10) 0.12133(6) 0.0237(3) Uani 1 1 d .
C3 C 0.02079(15) 0.61348(11) 0.14860(6) 0.0241(3) Uani 1 1 d .
H3B H 0.049(2) 0.6833(15) 0.1680(8) 0.032(4) Uiso 1 1 d .
H3A H -0.056(2) 0.6311(15) 0.1131(9) 0.033(4) Uiso 1 1 d .
C4 C -0.06149(15) 0.53925(11) 0.19496(6) 0.0239(3) Uani 1 1 d .
H4 H -0.156(2) 0.5740(14) 0.2065(8) 0.031(4) Uiso 1 1 d .
C5 C -0.10916(14) 0.42618(11) 0.16656(6) 0.0220(2) Uani 1 1 d .
C6 C 0.05194(14) 0.36732(10) 0.15256(6) 0.0193(2) Uani 1 1 d .
C7 C 0.14124(14) 0.35362(11) 0.21764(6) 0.0215(2) Uani 1 1 d .
C8 C 0.14481(17) 0.44683(12) 0.26278(6) 0.0270(3) Uani 1 1 d .
C9 C 0.04540(16) 0.52956(11) 0.25331(6) 0.0256(3) Uani 1 1 d .
H9 H 0.048(2) 0.5896(15) 0.2803(8) 0.029(4) Uiso 1 1 d .
C10 C 0.31179(15) 0.55915(11) 0.16687(6) 0.0256(3) Uani 1 1 d .
C11 C 0.48591(17) 0.66876(14) 0.22916(8) 0.0391(4) Uani 1 1 d .
H11A H 0.4914 0.6159 0.2640 0.059 Uiso 1 1 calc R
H11B H 0.4949 0.7435 0.2461 0.059 Uiso 1 1 calc R
H11C H 0.5721 0.6550 0.2014 0.059 Uiso 1 1 calc R
C12 C 0.21244(16) 0.62920(11) 0.06339(6) 0.0262(3) Uani 1 1 d .
H12B H 0.129(2) 0.6139(15) 0.0288(9) 0.035(5) Uiso 1 1 d .
H12A H 0.203(2) 0.7071(15) 0.0749(8) 0.033(4) Uiso 1 1 d .
C13 C 0.37335(17) 0.60451(13) 0.04217(7) 0.0301(3) Uani 1 1 d .
H13 H 0.392(2) 0.5302(16) 0.0296(9) 0.037(5) Uiso 1 1 d .
C14 C 0.4875(2) 0.67714(16) 0.04038(8) 0.0414(4) Uani 1 1 d .
H14B H 0.588(3) 0.6570(18) 0.0253(10) 0.053(6) Uiso 1 1 d .
H14A H 0.468(3) 0.7551(19) 0.0561(11) 0.056(6) Uiso 1 1 d .
C15 C -0.21641(16) 0.44283(13) 0.10694(7) 0.0281(3) Uani 1 1 d .
H15C H -0.161(2) 0.4784(16) 0.0738(9) 0.037(5) Uiso 1 1 d .
H15B H -0.257(2) 0.3729(17) 0.0901(9) 0.041(5) Uiso 1 1 d .
H15A H -0.304(2) 0.4869(16) 0.1189(9) 0.041(5) Uiso 1 1 d .
C16 C -0.20299(17) 0.36162(13) 0.21412(7) 0.0298(3) Uani 1 1 d .
H16C H -0.233(2) 0.2909(17) 0.1947(10) 0.045(5) Uiso 1 1 d .
H16B H -0.298(2) 0.4055(17) 0.2220(10) 0.046(5) Uiso 1 1 d .
H16A H -0.144(2) 0.3474(16) 0.2556(10) 0.046(5) Uiso 1 1 d .
C17 C 0.03435(15) 0.25100(11) 0.12273(6) 0.0228(3) Uani 1 1 d .
C18 C 0.17621(16) 0.18404(11) 0.10784(6) 0.0242(3) Uani 1 1 d .
C19 C 0.1490(2) 0.07365(12) 0.09367(8) 0.0358(3) Uani 1 1 d .
H19 H 0.046(3) 0.0489(17) 0.0937(10) 0.048(6) Uiso 1 1 d .
C20 C 0.2713(2) 0.00485(14) 0.07955(9) 0.0456(4) Uani 1 1 d .
H20 H 0.245(3) -0.070(2) 0.0685(12) 0.065(7) Uiso 1 1 d .
C21 C 0.4226(2) 0.04496(14) 0.07893(8) 0.0409(4) Uani 1 1 d .
H21 H 0.507(3) -0.0013(19) 0.0689(11) 0.059(6) Uiso 1 1 d .
C22 C 0.45189(18) 0.15427(14) 0.09330(7) 0.0342(3) Uani 1 1 d .
H22 H 0.560(2) 0.1832(16) 0.0940(9) 0.042(5) Uiso 1 1 d .
C23 C 0.32945(16) 0.22367(12) 0.10830(7) 0.0277(3) Uani 1 1 d .
H23 H 0.352(2) 0.2983(15) 0.1195(8) 0.031(4) Uiso 1 1 d .
C24 C 0.25972(18) 0.43950(13) 0.31972(7) 0.0304(3) Uani 1 1 d .
H24B H 0.362(2) 0.4226(16) 0.3063(9) 0.037(5) Uiso 1 1 d .
H24A H 0.267(2) 0.5097(16) 0.3394(9) 0.038(5) Uiso 1 1 d .
C25 C 0.21775(18) 0.35550(13) 0.36718(7) 0.0329(3) Uani 1 1 d .
H25 H 0.219(2) 0.2791(16) 0.3529(9) 0.035(5) Uiso 1 1 d .
C26 C 0.1866(2) 0.37743(19) 0.42600(8) 0.0439(4) Uani 1 1 d .
H26B H 0.164(3) 0.315(2) 0.4546(11) 0.059(6) Uiso 1 1 d .
H26A H 0.186(3) 0.449(2) 0.4415(11) 0.056(6) 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
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
C10 O4 C11 115.52(11)
O1 C1 C2 121.73(11)
O1 C1 C6 119.16(11)
C2 C1 C6 118.57(10)
C1 C2 C3 108.52(10)
C1 C2 C10 107.86(10)
C3 C2 C10 114.28(11)
C1 C2 C12 111.67(10)
C3 C2 C12 108.80(11)
C10 C2 C12 105.75(10)
C2 C3 C4 113.70(10)
C9 C4 C3 107.31(11)
C9 C4 C5 112.73(11)
C3 C4 C5 113.16(11)
C15 C5 C16 107.54(11)
C15 C5 C4 109.66(11)
C16 C5 C4 109.49(11)
C15 C5 C6 112.81(10)
C16 C5 C6 112.14(11)
C4 C5 C6 105.18(9)
C1 C6 C7 117.99(10)
C1 C6 C17 107.06(10)
C7 C6 C17 107.29(10)
C1 C6 C5 104.34(9)
C7 C6 C5 105.65(9)
C17 C6 C5 114.87(10)
O2 C7 C8 120.86(11)
O2 C7 C6 119.70(11)
C8 C7 C6 119.04(11)
C9 C8 C7 119.46(12)
C9 C8 C24 123.11(13)
C7 C8 C24 117.37(12)
C8 C9 C4 122.67(12)
O3 C10 O4 124.15(12)
O3 C10 C2 124.20(12)
O4 C10 C2 111.42(11)
C13 C12 C2 114.15(11)
C14 C13 C12 124.35(15)
O5 C17 C18 119.10(12)
O5 C17 C6 119.73(12)
C18 C17 C6 121.14(11)
C23 C18 C19 118.76(13)
C23 C18 C17 125.08(12)
C19 C18 C17 116.15(13)
C20 C19 C18 120.78(16)
C19 C20 C21 120.26(16)
C20 C21 C22 119.71(15)
C21 C22 C23 120.31(15)
C18 C23 C22 120.17(14)
C25 C24 C8 114.23(12)
C26 C25 C24 124.66(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2070(15)
O2 C7 1.2147(16)
O3 C10 1.2189(17)
O4 C10 1.3325(17)
O4 C11 1.4465(17)
O5 C17 1.2142(16)
C1 C2 1.5317(17)
C1 C6 1.5469(17)
C2 C3 1.5310(18)
C2 C10 1.5379(19)
C2 C12 1.5550(18)
C3 C4 1.5337(18)
C4 C9 1.5038(19)
C4 C5 1.5489(19)
C5 C15 1.5359(18)
C5 C16 1.5376(18)
C5 C6 1.5915(17)
C6 C7 1.5516(16)
C6 C17 1.5557(17)
C7 C8 1.4851(18)
C8 C9 1.325(2)
C8 C24 1.5187(19)
C12 C13 1.497(2)
C13 C14 1.317(2)
C17 C18 1.5063(18)
C18 C23 1.393(2)
C18 C19 1.394(2)
C19 C20 1.383(2)
C20 C21 1.380(3)
C21 C22 1.385(2)
C22 C23 1.393(2)
C24 C25 1.493(2)
C25 C26 1.318(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040133
