Mn-Catalyzed Electrochemical Chloroalkylation of Alkenes.
Fu, Niankai; Shen, Yifan; Allen, Anthony R.; Song, Lu; Ozaki, Atsushi; Lin, Song; ACS catalysis 9 (2019) 746–754; doi:10.1021/acscatal.8b03209

data_4515465
_publ_section_title
;
 Mn-Catalyzed Electrochemical Chloroalkylation of Alkenes.
;
_journal_issue                   1
_journal_name_full               'ACS catalysis'
_journal_page_first              746
_journal_page_last               754
_journal_paper_doi               10.1021/acscatal.8b03209
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C15 H15 Cl N2'
_chemical_formula_sum            'C15 H15 Cl N2'
_chemical_formula_weight         258.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-24
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2016.08.26 svn.r3337 for Rigaku Oxford Diffraction, GUI svn.r5221)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.0720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.47300(10)
_cell_length_b                   17.4446(3)
_cell_length_c                   9.03740(10)
_cell_measurement_reflns_used    9733
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6290
_cell_measurement_theta_min      5.5070
_cell_volume                     1332.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -39.00  81.00   0.50    0.10    --    0.00  57.00   0.00  240
  2  \w     94.00 151.00   0.50    0.50    --   62.87 121.00  49.00  114
  3  \w     95.00 178.00   0.50    0.50    --  125.75 121.00  49.00  166
  4  \w    100.00 178.00   0.50    0.50    --  125.75 111.00 150.00  156
  5  \w    100.00 178.00   0.50    0.50    --  125.75 111.00 120.00  156
  6  \w     99.00 125.00   0.50    0.50    --  125.75 178.00  60.00   52
  7  \w     91.00 150.00   0.50    0.50    --   62.87 125.00   0.00  118
  8  \w    100.00 178.00   0.50    0.50    --  125.75 111.00-120.00  156
  9  \w    123.00 149.00   0.50    0.50    --  125.75  77.00-180.00   52
 10  \w    100.00 178.00   0.50    0.50    --  125.75 111.00 -90.00  156
 11  \w     87.00 178.00   0.50    0.50    --  125.75  63.00 -90.00  182
 12  \w    119.00 145.00   0.50    0.50    --  125.75 -25.00  30.00   52
 13  \w     91.00 118.00   0.50    0.50    --  125.75 -25.00  30.00   54
 14  \w     62.00 178.00   0.50    0.50    --  125.75  37.00  30.00  232
 15  \w     75.00 149.00   0.50    0.50    --   62.87 152.00-151.00  148
 16  \w     80.00 178.00   0.50    0.50    --  125.75  77.00-120.00  196
 17  \w     74.00 169.00   0.50    0.50    --  125.75 152.00-151.00  190
 18  \w     80.00 178.00   0.50    0.50    --  125.75  77.00 -30.00  196
 19  \w     82.00 178.00   0.50    0.50    --  125.75  50.00 150.00  192
 20  \w     60.00 149.00   0.50    0.50    --  125.75 178.00 -30.00  178
 21  \w     60.00 149.00   0.50    0.50    --  125.75 178.00 -60.00  178
 22  \w     60.00 149.00   0.50    0.50    --  125.75 178.00 120.00  178
 23  \w     60.00 149.00   0.50    0.50    --  125.75 178.00  90.00  178
 24  \w     61.00 139.00   0.50    0.50    --  125.75 178.00 150.00  156
 25  \w     10.00  37.00   0.50    0.50    --   62.87  93.00  48.07   54
 26  \w      9.00  37.00   0.50    0.50    --   62.87  94.00-127.79   56
 27  \w     25.00 145.00   0.50    0.50    --   62.87  61.00-150.00  240
 28  \w     62.00 178.00   0.50    0.50    --  125.75  37.00-120.00  232
 29  \w    104.00 171.00   0.50    0.50    --  125.75 -76.00-172.92  134
 30  \w     79.00 110.00   0.50    0.50    --  125.75-111.00-120.00   62
 31  \w     71.00  97.00   0.50    0.50    --  125.75 -50.00 -90.00   52
 32  \w     67.00  93.00   0.50    0.50    --  125.75 -50.00 -60.00   52
 33  \w     82.00 113.00   0.50    0.50    --  125.75-110.00 -47.29   62
 34  \w     43.00 165.00   0.50    0.50    --  125.75 -63.00   0.00  244
 35  \w     82.00 109.00   0.50    0.50    --  125.75-111.00 120.00   54
 36  \w    100.00 133.00   0.50    0.50    --  125.75-148.00 155.55   66
 37  \w     45.00 135.00   0.50    0.50    --   62.87-152.00 167.00  180
 38  \w     45.00 135.00   0.50    0.50    --  125.75-152.00 167.00  180
 39  \w     43.00 165.00   0.50    0.50    --  125.75 -63.00 120.00  244
 40  \w     49.00  75.00   0.50    0.50    --  125.75 -25.00  30.00   52
 41  \w     33.00 178.00   0.50    0.50    --  125.75 -25.00 -30.00  290
 42  \w     39.00 119.00   0.50    0.50    --  125.75-121.00 -33.00  160
 43  \w     36.00 115.00   0.50    0.50    --  125.75-111.00   0.00  158
 44  \w     36.00 115.00   0.50    0.50    --  125.75-111.00 -90.00  158
 45  \w     36.00 115.00   0.50    0.50    --  125.75-111.00-150.00  158
 46  \w     36.00 115.00   0.50    0.50    --  125.75-111.00 -60.00  158
 47  \w     32.00 178.00   0.50    0.50    --  125.75 -91.00 -60.00  292
 48  \w     36.00 115.00   0.50    0.50    --  125.75-111.00 150.00  158
 49  \w     32.00 178.00   0.50    0.50    --  125.75 -91.00   0.00  292
 50  \w     36.00 115.00   0.50    0.50    --  125.75-111.00 -30.00  158
 51  \w     34.00 172.00   0.50    0.50    --  125.75 -77.00  90.00  276
 52  \w     42.00 171.00   0.50    0.50    --  125.75 -50.00  30.00  258
 53  \w     43.00  69.00   0.50    0.50    --  125.75 -50.00 -90.00   52
 54  \w     41.00  67.00   0.50    0.50    --  125.75 -77.00 -30.00   52
 55  \w     29.00 119.00   0.50    0.50    --   62.87-121.00 -33.00  180
 56  \w     32.00 178.00   0.50    0.50    --  125.75 -91.00 150.00  292
 57  \w     31.00  95.00   0.50    0.50    --  125.75 -12.00-150.00  128
 58  \w     -4.00  57.00   0.50    0.10    --    0.00 -99.00-150.00  122
 59  \w    -81.00  38.00   0.50    0.10    --    0.00 -57.00  30.00  238
 60  \w    -69.00  -7.00   0.50    0.10    --    0.00 121.00  49.00  124
 61  \w    -86.00 -25.00   0.50    0.10    --    0.00 152.00-151.00  122
 62  \w    -98.00 -36.00   0.50    0.10    --    0.00 178.00  30.00  124
 63  \w   -148.00 -14.00   0.50    0.50    --  -62.87 -45.00 -30.00  268
 64  \w   -148.00 -70.00   0.50    0.50    --  -62.87-125.00-120.00  156
 65  \w   -150.00 -73.00   0.50    0.50    --  -62.87-121.00 -33.00  154
 66  \w   -156.00 -80.00   0.50    0.50    --  -62.87 -94.00-150.00  152
 67  \w   -156.00 -80.00   0.50    0.50    --  -62.87 -94.00   0.00  152
 68  \w   -156.00 -80.00   0.50    0.50    --  -62.87 -94.00 -60.00  152
 69  \w   -156.00 -80.00   0.50    0.50    --  -62.87 -94.00  30.00  152
 70  \w   -151.00 -52.00   0.50    0.50    --  -62.87-152.00 167.00  198
 71  \w   -153.00 -52.00   0.50    0.50    -- -104.25-152.00 167.00  202
 72  \w   -176.00 -73.00   0.50    0.50    -- -104.25-121.00 -33.00  206
 73  \w   -177.00 -58.00   0.50    0.50    -- -104.25 -77.00-120.00  238
 74  \w   -177.00 -78.00   0.50    0.50    -- -104.25-111.00  90.00  198
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0304267000
_diffrn_orient_matrix_UB_12      0.0870552000
_diffrn_orient_matrix_UB_13      0.0074568000
_diffrn_orient_matrix_UB_21      -0.1593220000
_diffrn_orient_matrix_UB_22      0.0117572000
_diffrn_orient_matrix_UB_23      0.0690590000
_diffrn_orient_matrix_UB_31      0.0831324000
_diffrn_orient_matrix_UB_32      -0.0092240000
_diffrn_orient_matrix_UB_33      0.1561212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            23924
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.727
_diffrn_reflns_theta_min         5.071
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.453
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+1.2061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2322
_reflns_number_total             2413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03209_si_002.cif
_cod_data_source_block           rnf2_abs
_cod_database_code               4515465
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C15H15ClN2
_chemical_oxdiff_usercomment     'Crystallized from ether/hexanes.'
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
;
_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 1.629
_oxdiff_exptl_absorpt_empirical_full_min 0.703