Asymmetric CpxRh(III)-Catalyzed Acrylic Acid C‒H Functionalization with Allenes Provides Chiral γ-Lactones
Wang, Shou-Guo; Cramer, Nicolai; ACS Catalysis  (2020) 8231–8236; doi:10.1021/acscatal.0c02430

data_4517850
_publ_section_title
;
 Asymmetric CpxRh(III)-Catalyzed Acrylic Acid C--H Functionalization with
 Allenes Provides Chiral \g-Lactones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8231
_journal_page_last               8236
_journal_paper_doi               10.1021/acscatal.0c02430
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-12-13
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.53867(7)
_cell_length_b                   6.85703(6)
_cell_length_c                   35.6756(3)
_cell_measurement_reflns_used    16014
_cell_measurement_temperature    140.01(13)
_cell_measurement_theta_max      72.4530
_cell_measurement_theta_min      4.9340
_cell_volume                     1599.55(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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   -104.00 -65.00   1.00    4.00    --  -40.91-147.00 -87.00   39
  2  \w    -80.00  -5.00   1.00    4.00    --  -40.91 124.00 156.00   75
  3  \w    -84.00 -59.00   1.00    4.00    --  -40.91 147.00 -38.00   25
  4  \w     29.00  95.00   1.00    4.00    --   40.91-124.00  77.00   66
  5  \w     50.00  75.00   1.00    4.00    --   40.91-147.00 -87.00   25
  6  \w     83.00 113.00   1.00   16.00    --  105.15-147.00 -87.00   30
  7  \w    107.00 139.00   1.00   16.00    --  105.15 124.00 156.00   32
  8  \w    123.00 150.00   1.00   16.00    --  105.15 147.00 -38.00   27
  9  \w     55.00 112.00   1.00   16.00    --  105.15-124.00  77.00   57
 10  \w      0.00  30.00   1.00    4.00    --   34.00  83.00 166.04   30
 11  \w   -114.00 -16.00   1.00    4.00    --  -40.91 -38.00 -30.00   98
 12  \w   -114.00 -17.00   1.00    4.00    --  -40.91 -38.00-180.00   97
 13  \w      7.00  32.00   1.00    4.00    --   40.91  83.00 -99.01   25
 14  \w      8.00  39.00   1.00    4.00    --   40.91  77.00   5.23   31
 15  \w     14.00  40.00   1.00    4.00    --   46.00  76.00  76.26   26
 16  \w     12.00  39.00   1.00    4.00    --   46.00  81.00 -42.65   27
 17  \w     15.00  42.00   1.00    4.00    --   46.00  80.00 106.25   27
 18  \w     16.00  41.00   1.00    4.00    --   50.00  82.00-147.05   25
 19  \w     29.00  73.00   1.00    4.00    --   58.00  66.00  43.32   44
 20  \w     30.00  57.00   1.00    4.00    --   58.00  74.00 163.26   27
 21  \w     84.00 131.00   1.00    4.00    --   58.00  66.00  43.32   47
 22  \w     38.00  63.00   1.00    4.00    --   66.00  73.00-165.65   25
 23  \w     75.00 101.00   1.00    4.00    --   66.00  73.00 -85.70   26
 24  \w     34.00  68.00   1.00    4.00    --   66.00  73.00 -85.70   34
 25  \w     37.00  64.00   1.00    4.00    --   66.00  72.00-125.94   27
 26  \w     38.00  64.00   1.00    4.00    --   70.00  74.00  89.00   26
 27  \w     38.00  64.00   1.00    4.00    --   70.00  73.00 -39.40   26
 28  \w    101.00 126.00   1.00    4.00    --   70.00  73.00 -39.40   25
 29  \w     44.00  69.00   1.00    4.00    --   70.00  74.00  20.28   25
 30  \w    103.00 145.00   1.00    4.00    --   70.00  74.00  89.00   42
 31  \w    110.00 137.00   1.00   16.00    --   74.00  70.00 -71.57   27
 32  \w     43.00  81.00   1.00   16.00    --   74.00  71.00 119.04   38
 33  \w     43.00  73.00   1.00   16.00    --   74.00  70.00 -71.57   30
 34  \w     48.00  75.00   1.00   16.00    --   78.00  64.00 154.10   27
 35  \w     46.00  73.00   1.00   16.00    --   78.00  74.00-158.61   27
 36  \w     48.00  75.00   1.00   16.00    --   78.00  74.00 -29.96   27
 37  \w     60.00  86.00   1.00   16.00    --   86.00  64.00  29.50   26
 38  \w     56.00  99.00   1.00   16.00    --   86.00  68.00 152.73   43
 39  \w     60.00  95.00   1.00   16.00    --   90.00  66.00 -66.56   35
 40  \w     61.00  97.00   1.00   16.00    --   90.00  63.00  61.48   36
 41  \w    115.00 163.00   1.00   16.00    --   90.00  63.00  61.48   48
 42  \w    105.00 159.00   1.00   16.00    --   94.00  61.00-118.33   54
 43  \w     65.00 100.00   1.00   16.00    --   94.00  61.00-118.33   35
 44  \w     76.00 171.00   1.00   16.00    --  105.15  61.00 -90.00   95
 45  \w    135.00 167.00   1.00   16.00    --  105.15 111.00  90.00   32
 46  \w    118.00 176.00   1.00   16.00    --  105.15  61.00 -60.00   58
 47  \w     76.00 102.00   1.00   16.00    --  105.15  61.00 120.00   26
 48  \w     33.00 133.00   1.00   16.00    --  105.15 -61.00 120.00  100
 49  \w     77.00 104.00   1.00   16.00    --  105.15  61.00 -60.00   27
 50  \w    104.00 130.00   1.00   16.00    --  105.15 111.00  90.00   26
 51  \w     77.00 175.00   1.00   16.00    --  105.15  61.00 150.00   98
 52  \w     76.00 161.00   1.00   16.00    --  105.15  61.00-150.00   85
 53  \w    126.00 159.00   1.00   16.00    --  105.15  61.00 -30.00   33
 54  \w     36.00 109.00   1.00   16.00    --  105.15-111.00 120.00   73
 55  \w     77.00 104.00   1.00   16.00    --  105.15  61.00 -30.00   27
 56  \w     37.00 106.00   1.00   16.00    --  105.15-111.00 -60.00   69
 57  \w     77.00 120.00   1.00   16.00    --  105.15  61.00-180.00   43
 58  \w     76.00 160.00   1.00   16.00    --  105.15  61.00   0.00   84
 59  \w    116.00 176.00   1.00   16.00    --  105.15  61.00  90.00   60
 60  \w    137.00 178.00   1.00   16.00    --  105.15 111.00 120.00   41
 61  \w    146.00 174.00   1.00   16.00    --  105.15  61.00  60.00   28
 62  \w     76.00 111.00   1.00   16.00    --  105.15  61.00  90.00   35
 63  \w     76.00 144.00   1.00   16.00    --  105.15  61.00  60.00   68
 64  \w     79.00 166.00   1.00   16.00    --  106.00  70.00  18.03   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0484376000
_diffrn_orient_matrix_UB_12      -0.1943469000
_diffrn_orient_matrix_UB_13      -0.0197649000
_diffrn_orient_matrix_UB_21      0.0038302000
_diffrn_orient_matrix_UB_22      -0.1043613000
_diffrn_orient_matrix_UB_23      0.0382380000
_diffrn_orient_matrix_UB_31      -0.2305110000
_diffrn_orient_matrix_UB_32      -0.0426272000
_diffrn_orient_matrix_UB_33      -0.0035094000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            27684
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.849
_diffrn_reflns_theta_min         4.959
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.714
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1240 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0348P)^2^+0.2163P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3079
_reflns_number_total             3154
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c02430_si_002.cif
_cod_data_source_block           wsg3-4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4517850.cif.
;
_cod_database_code               4517850
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C20 H18 O2'
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.672
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H13A)=Sof(H13B)=Sof(H13C)=1-FVAR(1)
 Sof(H13D)=Sof(H13E)=Sof(H13F)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
3.b Disordered Me refined as rotating group:
 C13(H13A,H13B,H13C,H13D,H13E,H13F)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_shelx_res_checksum              34322
_shelx_hkl_checksum              11840
_olex2_date_sample_data_collection 2019-12-12
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.783