Stereochemical studies of the opening of chloro vinyl epoxides: cyclic chloronium ions as intermediates.
Shemet, Andrej; Sarlah, David; Carreira, Erick M.; Organic letters 17 (2015) 1878–1881; doi:10.1021/acs.orglett.5b00558

data_1554887
_publ_section_title
;
 Stereochemical studies of the opening of chloro vinyl epoxides: cyclic
 chloronium ions as intermediates.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1878
_journal_page_last               1881
_journal_paper_doi               10.1021/acs.orglett.5b00558
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 Br Cl N O3'
_chemical_formula_sum            'C13 H15 Br Cl N O3'
_chemical_formula_weight         348.62
_chemical_name_systematic        ca180213
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-02-26
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.12.05 svn.r2549, GUI svn.r4385)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.441(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8035(6)
_cell_length_b                   8.2644(10)
_cell_length_c                   18.363(2)
_cell_measurement_reflns_used    3677
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.70
_cell_volume                     726.79(15)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10365
_diffrn_reflns_theta_full        27.61
_diffrn_reflns_theta_max         27.61
_diffrn_reflns_theta_min         2.22
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.014
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0554 after correction.
The Ratio of minimum to maximum transmission is 0.8142.
The \l/2 correction factor is 0.0000.
;
_exptl_crystal_colour            '? colourless'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method hexane/DCM
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0267
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0010P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0424
_refine_ls_wR_factor_ref         0.0440
_reflns_number_gt                2898
_reflns_number_total             3344
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b00558_si_007.cif
_cod_data_source_block           mo_ca180213_0m
_cod_original_cell_volume        726.77(15)
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1554887
_olex2_refinement_description
;
1. Fixed Uiso
 At 1 times of:
  H3 of C3
2. Restrained distances
 N1-H1
 1.03 with sigma of 0.02
 C12-H12
 1.08 with sigma of 0.02
 C4-H4B = C3-H3 = C2-H2 = C1-H1B = C9-H9 = C10-H10 = C13-H13
 1.08 with sigma of 0.02
;