Enantioselective conjugate addition of hydroxylamines to α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal Rh(iii) complex
Deng, Tao; Thota, Ganesh Kumar; Li, Yi; Kang, Qiang; Organic Chemistry Frontiers 4 (2017) 573–; doi:10.1039/C6QO00865H

data_1553637
_publ_section_title
;
 Enantioselective conjugate addition of hydroxylamines to
 \a,\b-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal
 Rh(iii) complex
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              573
_journal_paper_doi               10.1039/C6QO00865H
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C16 H21 N3 O5'
_chemical_formula_weight         335.36
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-22 deposited with the CCDC.
2017-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.4855(4)
_cell_length_b                   15.8870(7)
_cell_length_c                   25.5299(13)
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      73.2840
_cell_measurement_theta_min      3.2680
_cell_volume                     3441.7(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41q (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0587
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8887
_diffrn_reflns_point_group_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.374
_diffrn_reflns_theta_min         3.276
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41q (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1564 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         5845
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0384
_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^)+(0.0300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.535
_reflns_Friedel_fraction_full    0.726
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                5040
_reflns_number_total             5845
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00865h2.cif
_cod_data_source_block           compound-1
_cod_database_code               1553637
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              88077
_shelx_hkl_checksum              95559