A Formal, One-Pot β-Chlorination of Primary Alcohols and Its Utilization in the Transformation of Terpene Feedstock and the Synthesis of a C2-Symmetrical Terminal Bis-Epoxide.
Swatschek, Jörg; Grothues, Lydia; Bauer, Jonathan O.; Strohmann, Carsten; Christmann, Mathias; The Journal of organic chemistry 79 (2014) 976–; doi:10.1021/jo402422b

data_4029008
_publ_section_title
;
 A Formal, One-Pot \b-Chlorination of Primary Alcohols and Its Utilization
 in the Transformation of Terpene Feedstock and the Synthesis of a
 C2-Symmetrical Terminal Bis-Epoxide.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              976
_journal_paper_doi               10.1021/jo402422b
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C7 H14 Cl2 O2'
_chemical_formula_sum            'C7 H14 Cl2 O2'
_chemical_formula_weight         201.08
_chemical_name_systematic        (2S,6S)-2,6-Dichloroheptane-1,7-diol
_space_group_IT_number           1
_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_date             2013-10-31T13:08:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                84.817(10)
_cell_angle_beta                 82.484(12)
_cell_angle_gamma                80.657(11)
_cell_formula_units_Z            1
_cell_length_a                   5.0136(8)
_cell_length_b                   5.3946(6)
_cell_length_c                   9.3077(13)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      3.84
_cell_volume                     245.65(6)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)'
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.37 (release 24-10-2008 CrysAlis171 .NET)
(compiled Oct 24 2008,09:44:38)
;
_computing_molecular_graphics
;
Ortep-3 (Farrugia, 1997) and Schakal 92
 (Keller 1992)
;
_computing_publication_material  'wingx (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur S Oxford Diffraction'
_diffrn_measurement_method       Omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3335
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.887
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd. Empirical absorption correction using
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             106
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         2123
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0331P)^2^+0.0268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.053
_refine_ls_wR_factor_ref         0.0533
_reflns_number_gt                2103
_reflns_number_total             2123
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402422b_si_001.cif
_cod_data_source_block           2538
_cod_database_code               4029008