Catalytic enantioselective arylative cyclizations of alkynyl 1,3-diketones by 1,4-rhodium(i) migration
Groves, Alistair; Sun, Jinwei; Parke, Hal R. I.; Callingham, Michael; Argent, Stephen P.; Taylor, Laurence J.; Lam, Hon Wai; Chemical Science 11 (2020) 2759–2764; doi:10.1039/C9SC06309A

data_1557263
_publ_section_title
;
 Catalytic enantioselective arylative cyclizations of alkynyl
 1,3-diketones by 1,4-rhodium(i) migration
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              2759
_journal_page_last               2764
_journal_paper_doi               10.1039/C9SC06309A
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.39
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-17 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5439(2)
_cell_length_b                   10.5734(2)
_cell_length_c                   17.3218(3)
_cell_measurement_reflns_used    14650
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      77.2300
_cell_measurement_theta_min      4.6370
_cell_volume                     1747.97(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      'N2 gas'
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'PILATUS3 R 200K Hybrid Pixel Array Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_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    -33.00  33.00   0.50    1.00    --    0.00 -82.00 120.00  132
  2  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00  60.00  132
  3  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00   0.00  132
  4  \w     13.00 129.00   0.50    4.00    --  102.40 -61.00-180.00  232
  5  \w     13.00  69.00   0.50    4.00    --  102.40 -30.00  30.00  112
  6  \w     13.00  69.00   0.50    4.00    --  102.40 -30.00   0.00  112
  7  \w     13.00  69.00   0.50    4.00    --  102.40 -30.00  60.00  112
  8  \w     13.00  77.00   0.50    4.00    --  102.40 -45.00 -60.00  128
  9  \w     13.00 136.00   0.50    4.00    --  102.40 -82.00-150.00  246
 10  \w     80.00 192.00   0.50    4.00    --  102.40  77.00  30.00  224
 11  \w     13.00  77.00   0.50    4.00    --  102.40 -45.00 150.00  128
 12  \w     65.00 192.00   0.50    4.00    --  102.40  15.00 -90.00  254
 13  \w     13.00 192.00   0.50    4.00    --  102.40   0.00-120.00  358
 14  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00-120.00  132
 15  \w    -33.00  33.00   0.50    1.00    --    0.00 -82.00 -60.00  132
 16  \w     78.00 192.00   0.50    4.00    --  102.40  30.00   0.00  228
 17  \w     13.00  81.00   0.50    4.00    --  102.40 -82.00  30.00  136
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'XtalLAB PRO MM007, PILATUS3 R 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628039000
_diffrn_orient_matrix_UB_12      -0.0388046000
_diffrn_orient_matrix_UB_13      -0.0783831000
_diffrn_orient_matrix_UB_21      -0.1232541000
_diffrn_orient_matrix_UB_22      -0.0645001000
_diffrn_orient_matrix_UB_23      0.0418290000
_diffrn_orient_matrix_UB_31      -0.0829352000
_diffrn_orient_matrix_UB_32      0.1249774000
_diffrn_orient_matrix_UB_33      -0.0027808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.788
_diffrn_reflns_theta_min         4.900
_diffrn_source                   'rotating anode'
_diffrn_source_type              'MicroMax 007 HF'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.210
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane/dichloromethane'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0780P)^2^+0.4869P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                3520
_reflns_number_total             3631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc06309a2.cif
_cod_data_source_block           aghwlb
_cod_depositor_comments
;Adding full bibliography for 1557262--1557263.cif.

 Adding full bibliography for 1557262--1557263.cif.
;
_cod_database_code               1557263
_nottingham_internal_coll_name   AGHWLB
_nottingham_internal_coll_number 17920
_nottingham_internal_coll_client AG/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '1.00, 4.00'
_nottingham_internal_coll_frame_width 0.50
_nottingham_internal_coll_user   pczlt
_nottingham_internal_coll_date   11/09/2018
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'XtalLAB PRO, A00000876'
_nottingham_internal_process_date 12/09/2018
_nottingham_internal_process_user pczlt
_nottingham_internal_solution_date 17/07/2019
_nottingham_internal_solution_user pczspa
_nottingham_internal_refinement_date 17/07/2019
_nottingham_internal_refinement_user pczspa
_nottingham_internal_validation_date 17/07/2019
_nottingham_internal_validation_user pczspa
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H22 O2'
_chemical_oxdiff_usercomment
'AGHWLB #17920 Crystal mounted on Micromount in fomblin for AG/HWL'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.869
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              47915
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_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 3.477
_oxdiff_exptl_absorpt_empirical_full_min 0.563