Enantioselective [4 + 1]-Annulation of α,β-Unsaturated Imines with Allylic Carbonates Catalyzed by a Hybrid P-Chiral Phosphine Oxide-Phosphine.
Li, Hanyuan; Luo, Jiesi; Li, Bojuan; Yi, Xizhen; He, Zhengjie; Organic letters 19 (2017) 5637–5640; doi:10.1021/acs.orglett.7b02800

data_1547528
_publ_section_title
;
 Enantioselective [4 + 1]-Annulation of \a,\b-Unsaturated Imines with
 Allylic Carbonates Catalyzed by a Hybrid P-Chiral Phosphine
 Oxide-Phosphine.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              5637
_journal_page_last               5640
_journal_paper_doi               10.1021/acs.orglett.7b02800
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H22 Br Cl N2 O6 S'
_chemical_formula_sum            'C27 H22 Br Cl N2 O6 S'
_chemical_formula_weight         617.88
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-10-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                100.941(9)
_cell_angle_beta                 98.338(15)
_cell_angle_gamma                93.200(11)
_cell_formula_units_Z            2
_cell_length_a                   7.762(6)
_cell_length_b                   12.126(9)
_cell_length_c                   14.580(12)
_cell_measurement_reflns_used    2177
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     1328.2(18)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11264
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         3.042
_exptl_absorpt_coefficient_mu    1.772
_exptl_absorpt_correction_T_max  0.8155
_exptl_absorpt_correction_T_min  0.7182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.257
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5770
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0714P)^2^+0.7390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1289
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4468
_reflns_number_total             5770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02800_si_004.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547527--1547529.cif.
;
_cod_original_cell_volume        1328.1(18)
_cod_database_code               1547528
_shelx_estimated_absorpt_t_max   0.815
_shelx_estimated_absorpt_t_min   0.718
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8), C17(H17), C18(H18), C20(H20),
 C21(H21), C23(H23), C24(H24), C26(H26), C27(H27)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              85431
_shelx_hkl_checksum              1977
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'