#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/34/4033402.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_4033402
loop_
_publ_author_name
'Krout, Michael R.'
'Henry, Christopher E.'
'Jensen, Thomas'
'Wu, Kun-Liang'
'Virgil, Scott C.'
'Stoltz, Brian M.'
_publ_section_title
;
 Wolff/Cope Approach to the AB Ring of the Sesterterpenoid Variecolin.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6995
_journal_page_last               7009
_journal_paper_doi               10.1021/acs.joc.7b02972
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C12 H16 O4'
_chemical_formula_sum            'C12 H16 O4'
_chemical_formula_weight         224.25
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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   difmap
_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                   6.3017(3)
_cell_length_b                   11.7387(5)
_cell_length_c                   14.4000(6)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.80
_cell_measurement_theta_min      3.31
_cell_volume                     1065.22(8)
_computing_cell_refinement       'Bruker SAINT-Plus v7.34A'
_computing_data_collection       'Bruker APEX2 v2.1-0'
_computing_data_reduction        'Bruker SAINT-Plus v7.34A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF 2008'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       'ω scans; 13 settings'
_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  0.1080
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            37096
_diffrn_reflns_theta_full        35.05
_diffrn_reflns_theta_max         35.05
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.899
_refine_ls_hydrogen_treatment    Unrestrained
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4514
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.899
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s²(Fo²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                4349
_reflns_number_total             4514
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b02972_si_002.cif
_cod_data_source_block           mrk03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_refine_ls_weighting_scheme' value 'Sigma' changed to 'sigma'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Difference Fourier map' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033402.cif.
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4033402
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
O1 O 0.37960(9) 0.08671(5) 0.14126(3) 0.01462(10) Uani 1 1 d
O2 O -0.13321(9) -0.09173(5) 0.20330(4) 0.01809(11) Uani 1 1 d
O3 O -0.04262(8) -0.11487(5) 0.35278(3) 0.01386(10) Uani 1 1 d
O4 O 0.24653(8) -0.22436(5) 0.39800(3) 0.01362(10) Uani 1 1 d
C1 C 0.27111(10) 0.09530(6) 0.37966(4) 0.01192(11) Uani 1 1 d
C2 C 0.30324(10) -0.03309(6) 0.35817(4) 0.01053(11) Uani 1 1 d
C3 C 0.20430(10) -0.01729(6) 0.25997(4) 0.01054(10) Uani 1 1 d
C4 C 0.18180(10) 0.11270(6) 0.27986(4) 0.01174(11) Uani 1 1 d
C5 C 0.36443(11) 0.16074(6) 0.22049(4) 0.01220(11) Uani 1 1 d
C6 C 0.56087(10) 0.15915(6) 0.28392(4) 0.01242(11) Uani 1 1 d
C7 C 0.47399(11) 0.16743(6) 0.38343(4) 0.01267(11) Uani 1 1 d
C8 C 0.63401(13) 0.13392(7) 0.45789(4) 0.01888(14) Uani 1 1 d
C9 C 0.33366(11) -0.02763(6) 0.17076(4) 0.01319(12) Uani 1 1 d
C10 C 0.15602(10) -0.11729(6) 0.40611(4) 0.01167(11) Uani 1 1 d
C11 C -0.00469(10) -0.07851(6) 0.26458(4) 0.01265(12) Uani 1 1 d
C12 C 0.13616(13) -0.31303(7) 0.44680(5) 0.01749(13) Uani 1 1 d
H1 H 0.1775(19) 0.1097(12) 0.4293(8) 0.021(3) Uiso 1 1 d
H2 H 0.4516(17) -0.0624(10) 0.3599(7) 0.011(2) Uiso 1 1 d
H4 H 0.0471(15) 0.1482(10) 0.2675(7) 0.009(2) Uiso 1 1 d
H5 H 0.3332(18) 0.2403(11) 0.1957(8) 0.019(3) Uiso 1 1 d
H6A H 0.6371(17) 0.0854(10) 0.2751(7) 0.016(2) Uiso 1 1 d
H6B H 0.6554(17) 0.2206(10) 0.2698(7) 0.013(2) Uiso 1 1 d
H7 H 0.4294(18) 0.2443(12) 0.3949(8) 0.022(3) Uiso 1 1 d
H8A H 0.574(2) 0.1409(13) 0.5221(9) 0.031(3) Uiso 1 1 d
H8B H 0.757(2) 0.1775(13) 0.4526(9) 0.031(3) Uiso 1 1 d
H8C H 0.686(2) 0.0555(13) 0.4490(9) 0.030(3) Uiso 1 1 d
H9A H 0.4588(18) -0.0661(10) 0.1802(7) 0.013(2) Uiso 1 1 d
H9B H 0.2564(18) -0.0681(10) 0.1225(8) 0.020(3) Uiso 1 1 d
H10 H 0.114(2) -0.0983(12) 0.4673(9) 0.025(3) Uiso 1 1 d
H12A H 0.118(2) -0.2961(12) 0.5127(9) 0.031(3) Uiso 1 1 d
H12B H 0.216(2) -0.3854(14) 0.4343(9) 0.034(3) Uiso 1 1 d
H12C H -0.009(2) -0.3258(13) 0.4249(8) 0.028(3) 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
C9 O1 C5 108.46(4)
C11 O3 C10 110.14(5)
C10 O4 C12 114.65(6)
C7 C1 C2 115.74(6)
C7 C1 C4 105.16(5)
C2 C1 C4 89.45(5)
C7 C1 H1 113.3(8)
C2 C1 H1 114.1(8)
C4 C1 H1 116.8(7)
C10 C2 C1 117.45(5)
C10 C2 C3 104.21(5)
C1 C2 C3 90.76(5)
C10 C2 H2 109.7(6)
C1 C2 H2 116.9(7)
C3 C2 H2 116.1(6)
C11 C3 C9 117.88(5)
C11 C3 C2 104.72(5)
C9 C3 C2 122.77(5)
C11 C3 C4 112.36(5)
C9 C3 C4 106.32(5)
C2 C3 C4 89.20(5)
C5 C4 C1 106.87(5)
C5 C4 C3 100.86(5)
C1 C4 C3 90.48(5)
C5 C4 H4 113.5(6)
C1 C4 H4 123.1(6)
C3 C4 H4 118.0(7)
O1 C5 C6 114.23(6)
O1 C5 C4 105.60(6)
C6 C5 C4 105.50(5)
O1 C5 H5 106.8(6)
C6 C5 H5 112.0(6)
C4 C5 H5 112.7(6)
C7 C6 C5 105.43(5)
C7 C6 H6A 110.2(6)
C5 C6 H6A 108.8(6)
C7 C6 H6B 111.8(6)
C5 C6 H6B 111.5(6)
H6A C6 H6B 109.1(8)
C8 C7 C1 115.71(6)
C8 C7 C6 113.83(6)
C1 C7 C6 103.23(5)
C8 C7 H7 108.4(7)
C1 C7 H7 106.3(7)
C6 C7 H7 108.9(7)
C7 C8 H8A 112.1(8)
C7 C8 H8B 110.6(8)
H8A C8 H8B 110.3(11)
C7 C8 H8C 111.7(7)
H8A C8 H8C 108.7(12)
H8B C8 H8C 103.0(11)
O1 C9 C3 106.39(5)
O1 C9 H9A 109.3(7)
C3 C9 H9A 111.9(7)
O1 C9 H9B 110.2(7)
C3 C9 H9B 111.9(7)
H9A C9 H9B 107.2(10)
O4 C10 O3 108.92(5)
O4 C10 C2 107.47(5)
O3 C10 C2 105.66(5)
O4 C10 H10 114.1(8)
O3 C10 H10 103.9(8)
C2 C10 H10 116.2(8)
O2 C11 O3 121.58(6)
O2 C11 C3 128.11(6)
O3 C11 C3 110.21(5)
O4 C12 H12A 112.8(8)
O4 C12 H12B 106.4(8)
H12A C12 H12B 114.0(11)
O4 C12 H12C 113.9(8)
H12A C12 H12C 103.4(11)
H12B C12 H12C 106.4(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.4372(9)
O1 C5 1.4374(8)
O2 C11 1.2077(8)
O3 C11 1.3610(7)
O3 C10 1.4689(8)
O4 C10 1.3853(9)
O4 C12 1.4356(9)
C1 C7 1.5344(9)
C1 C2 1.5518(10)
C1 C4 1.5569(8)
C1 H1 0.942(11)
C2 C10 1.5213(9)
C2 C3 1.5565(8)
C2 H2 0.997(11)
C3 C11 1.5018(9)
C3 C9 1.5263(8)
C3 C4 1.5590(10)
C4 C5 1.5406(9)
C4 H4 0.962(10)
C5 C6 1.5385(9)
C5 H5 1.020(12)
C6 C7 1.5370(8)
C6 H6A 0.998(12)
C6 H6B 0.957(11)
C7 C8 1.5237(10)
C7 H7 0.960(14)
C8 H8A 1.004(13)
C8 H8B 0.934(15)
C8 H8C 0.985(15)
C9 H9A 0.919(12)
C9 H9B 0.973(11)
C10 H10 0.947(13)
C12 H12A 0.977(13)
C12 H12B 1.005(16)
C12 H12C 0.982(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139095932
