#------------------------------------------------------------------------------
#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/21/4122141.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_4122141
loop_
_publ_author_name
'Plummer, Christopher W.'
'Wei, Carolyn S.'
'Yozwiak, Carrie E.'
'Soheili, Arash'
'Smithback, Sara O.'
'Leighton, James L.'
_publ_section_title
;
 Design, development, mechanistic elucidation, and rational optimization
 of a tandem ireland claisen/cope rearrangement reaction for rapid access
 to the (iso)cyclocitrinol core.
;
_journal_issue                   28
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9878
_journal_page_last               9881
_journal_paper_doi               10.1021/ja505131v
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C19 H26 O3'
_chemical_formula_weight         302.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.702(10)
_cell_angle_beta                 93.082(9)
_cell_angle_gamma                97.855(10)
_cell_formula_units_Z            2
_cell_length_a                   6.415(3)
_cell_length_b                   11.466(6)
_cell_length_c                   12.007(6)
_cell_measurement_reflns_used    787
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      3.10
_cell_volume                     813.4(7)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.1071
_diffrn_reflns_av_sigmaI/netI    0.2853
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4140
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9728
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2676
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.2172
_refine_ls_R_factor_gt           0.0718
_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)+(0.0423P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1511
_reflns_number_gt                989
_reflns_number_total             2676
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja505131v_si_002.cif
_cod_data_source_block           cpws10
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/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.

'_exptl_absorpt_correction_type' value 'EMPIRICAL'
changed to 'empirical' according to
/usr/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.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4122140--4122141.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4122141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.3501(6) 0.2701(3) -0.1041(3) 0.0276(11) Uani 1 1 d .
O2 O -0.1140(6) 0.5978(4) -0.1657(3) 0.0337(11) Uani 1 1 d .
O3 O 0.0256(7) 0.7344(4) 0.0165(3) 0.0293(11) Uani 1 1 d .
C1 C 0.0718(9) 0.9370(5) -0.1800(5) 0.0340(17) Uani 1 1 d .
H1A H 0.0170 0.8985 -0.2620 0.041 Uiso 1 1 calc R
H1B H 0.0258 1.0116 -0.1303 0.041 Uiso 1 1 calc R
C2 C 0.2112(9) 0.8869(5) -0.1351(5) 0.0273(16) Uani 1 1 d .
H2A H 0.2601 0.9296 -0.0525 0.033 Uiso 1 1 calc R
C3 C 0.3033(8) 0.7694(5) -0.1990(5) 0.0232(15) Uani 1 1 d .
C4 C 0.5446(8) 0.8130(5) -0.1921(5) 0.0299(15) Uani 1 1 d .
H4A H 0.5702 0.8714 -0.2347 0.045 Uiso 1 1 calc R
H4B H 0.6129 0.7393 -0.2290 0.045 Uiso 1 1 calc R
H4C H 0.6035 0.8559 -0.1080 0.045 Uiso 1 1 calc R
C5 C 0.2053(8) 0.7032(5) -0.3314(4) 0.0239(15) Uani 1 1 d .
H5A H 0.0491 0.6875 -0.3341 0.029 Uiso 1 1 calc R
H5B H 0.2426 0.7605 -0.3753 0.029 Uiso 1 1 calc R
C6 C 0.2813(9) 0.5781(5) -0.3942(5) 0.0249(15) Uani 1 1 d .
H6A H 0.2125 0.5396 -0.4777 0.030 Uiso 1 1 calc R
H6B H 0.4362 0.5943 -0.3970 0.030 Uiso 1 1 calc R
C7 C 0.2308(9) 0.4861(5) -0.3304(4) 0.0201(14) Uani 1 1 d .
H7A H 0.0736 0.4689 -0.3308 0.024 Uiso 1 1 calc R
C8 C 0.3057(9) 0.3612(5) -0.3850(4) 0.0209(15) Uani 1 1 d .
C9 C 0.1746(9) 0.2524(5) -0.4457(4) 0.0242(15) Uani 1 1 d .
H9A H 0.0298 0.2551 -0.4641 0.029 Uiso 1 1 calc R
C10 C 0.2495(9) 0.1240(5) -0.4865(4) 0.0265(15) Uani 1 1 d .
H10A H 0.1324 0.0585 -0.5382 0.032 Uiso 1 1 calc R
H10B H 0.3683 0.1269 -0.5352 0.032 Uiso 1 1 calc R
C11 C 0.3215(9) 0.0860(5) -0.3826(5) 0.0277(15) Uani 1 1 d .
H11A H 0.3316 -0.0051 -0.4155 0.033 Uiso 1 1 calc R
H11B H 0.2096 0.0962 -0.3279 0.033 Uiso 1 1 calc R
C12 C 0.5316(9) 0.1575(5) -0.3082(5) 0.0288(15) Uani 1 1 d .
H12A H 0.6472 0.1369 -0.3596 0.035 Uiso 1 1 calc R
H12B H 0.5542 0.1263 -0.2422 0.035 Uiso 1 1 calc R
C13 C 0.5496(8) 0.3029(5) -0.2536(5) 0.0203(14) Uani 1 1 d .
H13A H 0.6941 0.3370 -0.2088 0.024 Uiso 1 1 calc R
C14 C 0.5348(9) 0.3595(5) -0.3539(4) 0.0218(14) Uani 1 1 d .
H14A H 0.6161 0.4465 -0.3253 0.026 Uiso 1 1 calc R
H14B H 0.5947 0.3073 -0.4255 0.026 Uiso 1 1 calc R
C15 C 0.3911(8) 0.3390(5) -0.1622(5) 0.0183(14) Uani 1 1 d .
C16 C 0.2863(9) 0.4547(5) -0.1320(4) 0.0238(15) Uani 1 1 d .
H16A H 0.3235 0.5035 -0.0452 0.029 Uiso 1 1 calc R
H16B H 0.1315 0.4251 -0.1444 0.029 Uiso 1 1 calc R
C17 C 0.3313(8) 0.5481(5) -0.1971(4) 0.0177(14) Uani 1 1 d .
H17A H 0.4882 0.5644 -0.1984 0.021 Uiso 1 1 calc R
C18 C 0.2651(8) 0.6758(5) -0.1309(5) 0.0213(15) Uani 1 1 d .
H18A H 0.3594 0.7149 -0.0535 0.026 Uiso 1 1 calc R
C19 C 0.0403(9) 0.6637(5) -0.0982(5) 0.0234(15) Uani 1 1 d .
H1 H -0.118(11) 0.736(6) 0.035(6) 0.09(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
C1 C2 C3 127.8(5)
C2 C3 C4 106.3(4)
C2 C3 C5 112.0(4)
C4 C3 C5 110.5(4)
C2 C3 C18 109.1(4)
C4 C3 C18 108.8(4)
C5 C3 C18 109.9(4)
C6 C5 C3 112.7(4)
C7 C6 C5 111.7(4)
C8 C7 C6 115.1(4)
C8 C7 C17 107.9(4)
C6 C7 C17 109.6(4)
C9 C8 C14 119.8(5)
C9 C8 C7 123.3(5)
C14 C8 C7 116.4(5)
C8 C9 C10 122.5(5)
C11 C10 C9 113.4(4)
C10 C11 C12 117.3(5)
C11 C12 C13 115.5(4)
C15 C13 C12 109.9(4)
C15 C13 C14 114.8(4)
C12 C13 C14 111.0(4)
C8 C14 C13 108.1(4)
O1 C15 C16 116.7(5)
O1 C15 C13 117.5(5)
C16 C15 C13 125.8(5)
C15 C16 C17 120.6(5)
C18 C17 C16 112.5(4)
C18 C17 C7 113.0(4)
C16 C17 C7 110.2(4)
C19 C18 C17 113.1(5)
C19 C18 C3 111.4(4)
C17 C18 C3 112.6(4)
O2 C19 O3 122.0(5)
O2 C19 C18 125.4(5)
O3 C19 C18 112.6(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.237(6)
O2 C19 1.218(6)
O3 C19 1.344(6)
C1 C2 1.314(7)
C2 C3 1.513(7)
C3 C4 1.549(7)
C3 C5 1.551(7)
C3 C18 1.566(7)
C5 C6 1.527(7)
C6 C7 1.519(7)
C7 C8 1.506(7)
C7 C17 1.563(6)
C8 C9 1.341(7)
C8 C14 1.501(7)
C9 C10 1.532(7)
C10 C11 1.528(6)
C11 C12 1.529(7)
C12 C13 1.546(7)
C13 C15 1.524(7)
C13 C14 1.561(6)
C15 C16 1.508(7)
C16 C17 1.541(6)
C17 C18 1.530(7)
C18 C19 1.516(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139123320
