Iridium(iii)-bis(imidazolinyl)phenyl catalysts for enantioselective C–H functionalization with ethyl diazoacetate
Weldy, N. Mace; Schafer, A. G.; Owens, C. P.; Herting, C. J.; Varela-Alvarez, A.; Chen, S.; Niemeyer, Z.; Musaev, D. G.; Sigman, M. S.; Davies, H. M. L.; Blakey, S. B.; Chem. Sci. 7 (2016) 3142–; doi:10.1039/C6SC00190D

data_1542408
_publ_section_title
;
 Iridium(iii)-bis(imidazolinyl)phenyl catalysts for enantioselective C--H
 functionalization with ethyl diazoacetate
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3142
_journal_paper_doi               10.1039/C6SC00190D
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_chemical_name_systematic
'4-methoxyphenyl 1,3-dihydro-2-benzofuran-1-ylacetate'
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-12-10
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-06-22 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.47301(10)
_cell_length_b                   12.08020(15)
_cell_length_c                   15.6344(2)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.356
_cell_measurement_theta_min      5.660
_cell_volume                     1411.40(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24525
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.349
_diffrn_reflns_theta_min         4.626
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7537
_exptl_absorpt_correction_T_min  0.7079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0457 before and 0.0381 after correction.
The Ratio of minimum to maximum transmission is 0.9392.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.176
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1144 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2805
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0270
_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^)+(0.0383P)^2^+0.2484P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0670
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2766
_reflns_number_total             2805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc00190d2.cif
_cod_data_source_block           ngm-v-215
_cod_depositor_comments          'Adding full bibliography for 1542408.cif.'
_cod_database_code               1542408
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.841
_olex2_refinement_description
;
1. Restrained distances
 C9-H9B
 1 with sigma of 0.01
 C4-H4
 1 with sigma of 0.01
 C5-H5
 0.975 with sigma of 0.02
 C5-H5
 0.99 with sigma of 0.01
 C9-H9A \\sim C9-H9B
 with sigma of 0.005
 C5-H5 \\sim C6-H6 \\sim C7-H7 \\sim C8-H8 \\sim C12-H12 \\sim C13-H13 \\sim
C16-H16 \\sim C15-H15
 with sigma of 0.005
 C17-H17A \\sim C17-H17B \\sim C17-H17C
 with sigma of 0.005
2. Uiso/Uaniso restraints and constraints
Uiso(H4) = Uiso(H9B) = Uiso(H9A)
Uiso(H8) = Uiso(H7) = Uiso(H6) = Uiso(H5) = Uiso(H12) = Uiso(H13) = Uiso(H16) =
Uiso(H15)
Uiso(H1B) = Uiso(H1A)
Uiso(H17A) = Uiso(H17B) = Uiso(H17C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id NGM-V-215
_olex2_submission_special_instructions 'No special instructions were received'