Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols.
Phipps, Erik J. T.; Rovis, Tomislav; Journal of the American Chemical Society 141 (2019) 6807–6811; doi:10.1021/jacs.9b02156

data_4128103
_publ_section_title
;
 Rh(III)-Catalyzed C-H Activation-Initiated Directed Cyclopropanation of
 Allylic Alcohols.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6807
_journal_page_last               6811
_journal_paper_doi               10.1021/jacs.9b02156
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.386(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.0490(6)
_cell_length_b                   5.46156(14)
_cell_length_c                   25.6163(8)
_cell_measurement_reflns_used    4926
_cell_measurement_temperature    100.2(4)
_cell_measurement_theta_max      72.6700
_cell_measurement_theta_min      4.5940
_cell_volume                     2676.81(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.2(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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    -79.00  -7.00   1.00    5.00    --  -64.00  19.00  30.00   72
  2  \w    -79.00  -7.00   1.00    5.00    --  -64.00  19.00 120.00   72
  3  \w     27.00  97.00   1.00    1.00    --   67.35 -99.00  90.00   70
  4  \w    -60.00  32.00   1.00    1.00    --  -37.78  19.00-180.00   92
  5  \w    -55.00  26.00   1.00    1.00    --  -37.78  37.00 -90.00   81
  6  \w     -9.00  26.00   1.00    1.00    --  -37.78  57.00   0.00   35
  7  \w     69.00  94.00   1.00    1.00    --   37.78 178.00 -30.00   25
  8  \w     60.00  93.00   1.00    1.00    --   37.78 178.00 -60.00   33
  9  \w     28.00  70.00   1.00    1.00    --   37.78 -99.00 -30.00   42
 10  \w     65.00 108.00   1.00    5.00    --  111.00 -94.00-180.00   43
 11  \w     83.00 108.00   1.00    5.00    --  111.00 -94.00   0.00   25
 12  \w     44.00  98.00   1.00    5.00    --  111.00 -45.00  90.00   54
 13  \w     91.00 117.00   1.00    5.00    --  111.00 -61.00  60.00   26
 14  \w     46.00  81.00   1.00    5.00    --  111.00 -61.00 150.00   35
 15  \w     50.00 102.00   1.00    5.00    --  111.00 -45.00 -90.00   52
 16  \w     51.00 104.00   1.00    5.00    --  111.00-111.00 150.00   53
 17  \w     58.00 102.00   1.00    5.00    --  111.00 -94.00-120.00   44
 18  \w    102.00 139.00   1.00    5.00    --  111.00  61.00   0.00   37
 19  \w    123.00 172.00   1.00    5.00    --  111.00  15.00   0.00   49
 20  \w     92.00 144.00   1.00    5.00    --  111.00 -15.00  90.00   52
 21  \w     47.00  85.00   1.00    5.00    --  111.00 -30.00-180.00   38
 22  \w    135.00 161.00   1.00    5.00    --  111.00  30.00 150.00   26
 23  \w     91.00 118.00   1.00    5.00    --  111.00  77.00  60.00   27
 24  \w    102.00 142.00   1.00    5.00    --  111.00  30.00 -60.00   40
 25  \w    100.00 141.00   1.00    5.00    --  111.00 111.00 -90.00   41
 26  \w     64.00  90.00   1.00    5.00    --  111.00 -15.00  90.00   26
 27  \w     51.00  88.00   1.00    5.00    --  111.00 -94.00  60.00   37
 28  \w    147.00 172.00   1.00    5.00    --  111.00 111.00  60.00   25
 29  \w    100.00 126.00   1.00    5.00    --  111.00  45.00   0.00   26
 30  \w     68.00 113.00   1.00    5.00    --  111.00 -61.00 -60.00   45
 31  \w     90.00 115.00   1.00    5.00    --  111.00  30.00  60.00   25
 32  \w    150.00 176.00   1.00    5.00    --  111.00  30.00  60.00   26
 33  \w     88.00 118.00   1.00    5.00    --  111.00 -30.00  60.00   30
 34  \w    144.00 178.00   1.00    5.00    --  111.00  30.00 120.00   34
 35  \w    106.00 141.00   1.00    5.00    --  111.00  30.00 120.00   35
 36  \w    134.00 175.00   1.00    5.00    --  111.00  45.00-150.00   41
 37  \w     87.00 129.00   1.00    5.00    --  111.00 -61.00   0.00   42
 38  \w     44.00  72.00   1.00    5.00    --  111.00 -61.00   0.00   28
 39  \w     90.00 121.00   1.00    5.00    --  111.00 -30.00-180.00   31
 40  \w    101.00 126.00   1.00    5.00    --  111.00  45.00-150.00   25
 41  \w     93.00 119.00   1.00    5.00    --  111.00  30.00 150.00   26
 42  \w    134.00 160.00   1.00    5.00    --  111.00 111.00-180.00   26
 43  \w     54.00  79.00   1.00    5.00    --  111.00-111.00-150.00   25
 44  \w    153.00 178.00   1.00    5.00    --  111.00  45.00-120.00   25
 45  \w     58.00  86.00   1.00    5.00    --  111.00 -45.00 150.00   28
 46  \w     56.00  97.00   1.00    5.00    --  111.00 -94.00  90.00   41
 47  \w     47.00 125.00   1.00    5.00    --  111.00 -64.00-145.98   78
 48  \w    103.00 128.00   1.00    5.00    --  111.00 178.00 -60.00   25
 49  \w     56.00 120.00   1.00    5.00    --  111.00 -82.00 -98.24   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0505377000
_diffrn_orient_matrix_UB_12      -0.0118722000
_diffrn_orient_matrix_UB_13      0.0349369000
_diffrn_orient_matrix_UB_21      -0.0626281000
_diffrn_orient_matrix_UB_22      -0.0005608000
_diffrn_orient_matrix_UB_23      -0.0524471000
_diffrn_orient_matrix_UB_31      0.0022579000
_diffrn_orient_matrix_UB_32      -0.2817997000
_diffrn_orient_matrix_UB_33      -0.0013380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12900
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.839
_diffrn_reflns_theta_min         3.616
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.683
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0581P)^2^+2.1312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2666
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b02156_si_002.cif
_cod_data_source_block           ejtp2213b
_cod_original_cell_volume        2676.80(14)
_cod_database_code               4128103
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C17 H16 O2'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     51.74
_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), C2(H2), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              36141
_shelx_hkl_checksum              95130
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.470
_oxdiff_exptl_absorpt_empirical_full_min 0.825