Iron(ii)-catalyzed asymmetric intramolecular olefin aminochlorination using chloride ion
Zhu, Cheng-Liang; Tian, Jun-Shan; Gu, Zhen-Yuan; Xing, Guo-Wen; Xu, Hao; Chem. Sci. 6 (2015) 3044–; doi:10.1039/C5SC00221D

data_1518846
_publ_section_title
;
 Iron(ii)-catalyzed asymmetric intramolecular olefin aminochlorination
 using chloride ion
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3044
_journal_paper_doi               10.1039/C5SC00221D
_journal_volume                  6
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H9 Br Cl N O2'
_chemical_formula_sum            'C10 H9 Br Cl N O2'
_chemical_formula_weight         290.54
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2014-10-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.16 svn.r3037 for OlexSys, GUI svn.r4914)
;
_audit_update_record
;
2015-01-02 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.944(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9280(4)
_cell_length_b                   7.6682(5)
_cell_length_c                   11.3533(8)
_cell_measurement_reflns_used    6218
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      30.454
_cell_measurement_theta_min      2.656
_cell_volume                     513.31(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.1-1 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_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  0.0271
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5260
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         3.211
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.240
_exptl_absorpt_correction_T_max  0.6856
_exptl_absorpt_correction_T_min  0.4762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0804 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.6946.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_description       prism
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.074(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2561
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0540
_refine_ls_wR_factor_ref         0.0544
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                2404
_reflns_number_total             2561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc00221d2.cif
_cod_data_source_block           czhu-para-br-acl
_cod_depositor_comments          'Adding full bibliography for 1518846.cif.'
_cod_database_code               1518846
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.592
_shelx_estimated_absorpt_t_min   0.343
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1
 0.975 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C9(H9), C7(H7)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id czhu-para-br-acl
_olex2_submission_special_instructions 'No special instructions were received'