Synthesis of sesquiterpene-inspired derivatives designed for covalent binding and their inhibition of the NF-κB pathway.
Duplan, Vincent; Serba, Christelle; Garcia, Jose; Valot, Gaëlle; Barluenga, Sofia; Hoerlé, Mélanie; Cuendet, Muriel; Winssinger, Nicolas; Organic & biomolecular chemistry 12 (2014) 370–375; doi:10.1039/c3ob42049c

data_7153558
_publ_section_title
;
 Synthesis of sesquiterpene-inspired derivatives designed for covalent
 binding and their inhibition of the NF-\kB pathway.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              370
_journal_page_last               375
_journal_paper_doi               10.1039/c3ob42049c
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C12 H20 O3, 0.5(H2 O)'
_chemical_formula_sum            'C12 H21 O3.5'
_chemical_formula_weight         221.29
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 108.536(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.6423(13)
_cell_length_b                   6.0433(3)
_cell_length_c                   16.8338(9)
_cell_measurement_reflns_used    2620
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      3.35
_cell_volume                     2473.3(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, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8412
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0386
_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/[\s^2^(Fo^2^)+(0.0529P)^2^+0.9210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1034
_reflns_number_gt                2152
_reflns_number_total             2835
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c3ob42049c.txt
_cod_data_source_block           nwsb100723
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/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 

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_moiety     '2(C12 H20 O3), H2 O'
_cod_original_formula_sum        'C24 H42 O7'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     442.58
_cod_database_code               7153558