Asymmetric synthesis and biological evaluation of natural or bioinspired cytotoxic c2-symmetrical lipids with two terminal chiral alkynylcarbinol pharmacophores.
Listunov, Dymytrii; Fabing, Isabelle; Saffon-Merceron, Nathalie; Gaspard, Hafida; Volovenko, Yulian; Maraval, Valérie; Chauvin, Remi; Génisson, Yves; The Journal of organic chemistry 80 (2015) 5386–5394; doi:10.1021/acs.joc.5b00494

data_4031008
_publ_section_title
;
 Asymmetric synthesis and biological evaluation of natural or bioinspired
 cytotoxic c2-symmetrical lipids with two terminal chiral alkynylcarbinol
 pharmacophores.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5386
_journal_page_last               5394
_journal_paper_doi               10.1021/acs.joc.5b00494
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C40 H63 N O2 Si'
_chemical_formula_weight         618.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.439(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.139(5)
_cell_length_b                   7.1275(15)
_cell_length_c                   23.454(5)
_cell_measurement_reflns_used    1849
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      16.81
_cell_measurement_theta_min      3.74
_cell_volume                     3843.7(14)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker kappa APEX-II CCD Quazar'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1282
_diffrn_reflns_av_unetI/netI     0.1540
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29492
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         5.218
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.068
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.08(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6571
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0653
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.1166P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                3566
_reflns_number_total             6571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00494_si_002.cif
_cod_data_source_block           12
_cod_depositor_comments
'Adding full bibliography for 4031008--4031009.cif.'
_cod_original_cell_volume        3843.8(14)
_cod_database_code               4031008
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.998
_shelxl_version_number           2014/6
_shelx_res_checksum              30055
_shelx_hkl_checksum              75889