Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation.
Ayala, Caitlan E.; Villalpando, Andres; Nguyen, Alex L.; McCandless, Gregory T.; Kartika, Rendy; Organic letters 14 (2012) 3676–3679; doi:10.1021/ol301520d

data_1508299
_publ_section_title
;
 Chlorination of aliphatic primary alcohols via triphosgene-triethylamine
 activation.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3676
_journal_page_last               3679
_journal_paper_doi               10.1021/ol301520d
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H15 Cl O'
_chemical_formula_sum            'C15 H15 Cl O'
_chemical_formula_weight         246.72
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_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_audit_update_record
;
2012-04-02 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.379(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6724(12)
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_cell_length_c                   11.9146(16)
_cell_measurement_reflns_used    1933
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_cell_measurement_theta_min      5.22
_cell_volume                     1248.3(3)
_computing_cell_refinement       'Bruker SAINT'
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'SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type
;
Bruker Kappa Apex-II CCD area detector diffractometer (with an Oxford
Cryosystems cryostream cooler)
;
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
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_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
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_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0648P)^2^+0.1678P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1051
_reflns_number_gt                1803
_reflns_number_total             2207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol301520d_si_003.cif
_cod_data_source_block           Revised_Rendy1
_cod_depositor_comments
'Adding full bibliography for 1508299--1508300.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1508299