Synthesis of Malhamensilipin A Exploiting Iterative Epoxidation/Chlorination: Experimental and Computational Analysis of Epoxide-Derived Chloronium Ions
Saska, Jan; Lewis, William; Paton, Robert; Denton, Ross Matthew; Chem. Sci.  (2016) –; doi:10.1039/C6SC03012B

data_1543763
_publ_section_title
;
 Synthesis of Malhamensilipin A Exploiting Iterative
 Epoxidation/Chlorination: Experimental and Computational Analysis of
 Epoxide-Derived Chloronium Ions
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C6SC03012B
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H29 Cl3 O3'
_chemical_formula_sum            'C17 H29 Cl3 O3'
_chemical_formula_weight         387.75
_space_group_IT_number           19
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL-97 created file'
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1865(3)
_cell_length_b                   9.3623(5)
_cell_length_c                   40.6608(18)
_cell_measurement_reflns_used    4779
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.37
_cell_measurement_theta_min      3.26
_cell_volume                     1974.39(18)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    ' ? '
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            10046
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.54
_diffrn_reflns_theta_min         4.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.291
_exptl_absorpt_correction_T_max  1.096
_exptl_absorpt_correction_T_min  0.3
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.4221
_exptl_crystal_size_mid          0.0789
_exptl_crystal_size_min          0.0506
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1503 Friedel pairs measured'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0638
_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^)+(0.0055P)^2^+8.0722P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                3563
_reflns_number_total             3919
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c6sc03012b2.cif
_cod_data_source_block           JSRDCC
_cod_original_cell_volume        1974.38(17)
_cod_database_code               1543763
_nottingham_internal_coll_name   JSRDCC
_nottingham_internal_coll_number 10309
_nottingham_internal_coll_client JS/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '30 and 120'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   wl
_nottingham_internal_coll_date   30/3/2011
_nottingham_internal_process_user wl
_nottingham_internal_process_date 31/03/2011
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 31/3/2011
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 31/3/2011
_nottingham_internal_validation_user wl
_nottingham_internal_validation_date 1/4/2011
_nottingham_internal_archive_date 1/4/2011