Radical-mediated intramolecular β-C(sp<sup>3</sup>)-H amidation of alkylimidates: facile synthesis of 1,2-amino alcohols.
Mou, Xue-Qing; Chen, Xiang-Yu; Chen, Gong; He, Gang; Chemical communications (Cambridge, England) 54 (2018) 515–518; doi:10.1039/c7cc08897c

data_7121000
_publ_section_title
;
 Radical-mediated intramolecular \b-C(sp<sup>3</sup>)-H amidation of
 alkylimidates: facile synthesis of 1,2-amino alcohols.
;
_journal_issue                   5
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              515
_journal_page_last               518
_journal_paper_doi               10.1039/c7cc08897c
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C12 H14 Cl3 I2 N O'
_chemical_formula_sum            'C12 H14 Cl3 I2 N O'
_chemical_formula_weight         548.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-02-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-07-12 deposited with the CCDC.
2017-12-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.469(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7496(5)
_cell_length_b                   10.1118(3)
_cell_length_c                   12.9485(4)
_cell_measurement_reflns_used    5767
_cell_measurement_temperature    298(10)
_cell_measurement_theta_max      28.4510
_cell_measurement_theta_min      3.6880
_cell_volume                     1658.71(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      6.00  36.00   1.00    2.50    --   18.94 -57.00 -60.00   30
  2  \w      1.00  57.00   1.00    2.50    --   18.94 -99.00 -90.00   56
  3  \w    -46.00 -20.00   1.00    2.50    --   18.94 -77.00  60.00   26
  4  \w    -63.00  31.00   1.00    2.50    --  -19.25  19.00   0.00   94
  5  \w    -10.00  78.00   1.00    2.50    --   18.94  77.00  60.00   88
  6  \w     -9.00  86.00   1.00    2.50    --   18.94  77.00-180.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0503151000
_diffrn_orient_matrix_UB_12      0.0210403000
_diffrn_orient_matrix_UB_13      -0.0120388000
_diffrn_orient_matrix_UB_21      0.0223303000
_diffrn_orient_matrix_UB_22      -0.0604627000
_diffrn_orient_matrix_UB_23      0.0195808000
_diffrn_orient_matrix_UB_31      -0.0102647000
_diffrn_orient_matrix_UB_32      -0.0286600000
_diffrn_orient_matrix_UB_33      -0.0501007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10264
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.929
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.267
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.196
_exptl_crystal_description       block
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     22
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0402P)^2^+2.0503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0870
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2555
_reflns_number_total             2881
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc08897c2.cif
_cod_data_source_block           p170209c
_cod_depositor_comments
'Adding full bibliography for 7120999--7121000.cif.'
_cod_original_cell_volume        1658.71(9)
_cod_database_code               7121000
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H O N I'
_chemical_oxdiff_usercomment     MXQ-1-1-128
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 0.86 with sigma of 0.005
3. Rigid bond restraints
 Cl1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, Cl3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim Cl1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C1 \\sim Cl3: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
Cl2 \\sim C1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
5.a Ternary CH refined with riding coordinates:
 C3(H3), C6(H6), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C5(H5A,H5B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B)
;
_olex2_date_sample_data_collection 1486652000.67
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.389
_oxdiff_exptl_absorpt_empirical_full_min 0.601