A Bifunctional Iminophosphorane Squaramide Catalyzed Enantioselective Synthesis of Hydroquinazolines via Intramolecular Aza-Michael Reaction to α,β-Unsaturated Esters
su, guanglong; Thompson, Connor J.; Yamazaki, Ken; Rozsar, Daniel; Christensen, Kirsten; Hamlin, Trevor A.; Dixon, Darren; Chemical Science  (2021) –; doi:10.1039/D1SC00856K

data_1561134
_publ_section_title
;
 A Bifunctional Iminophosphorane Squaramide Catalyzed Enantioselective
 Synthesis of Hydroquinazolines via Intramolecular Aza-Michael Reaction to
 \a,\b-Unsaturated Esters
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC00856K
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H21 I N2 O3'
_chemical_formula_sum            'C20 H21 I N2 O3'
_chemical_formula_weight         464.30
_chemical_melting_point          ?
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2020-11-05
_audit_creation_method           'CRYSTALS_ver_14.61_build_7903 '
_audit_update_record
;
2021-01-07 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8204(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.46500(10)
_cell_length_b                   9.55400(10)
_cell_length_c                   15.72860(10)
_cell_measurement_reflns_used    17367
_cell_measurement_temperature    150
_cell_measurement_theta_max      76.64
_cell_measurement_theta_min      2.82
_cell_volume                     2018.90(3)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_av_unetI/netI     0.034
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22597
_diffrn_reflns_theta_full        75.043
_diffrn_reflns_theta_max         76.574
_diffrn_reflns_theta_min         2.816
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    12.635
_exptl_absorpt_correction_T_max  0.36
_exptl_absorpt_correction_T_min  0.03
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.58
_refine_diff_density_min         -0.66
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0586
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         8251
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0748
_refine_ls_shift/su_max          0.0005529
_refine_ls_shift/su_mean         0.0000175
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.15P)^2^ + 0.21P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1746
_refine_ls_wR_factor_gt          0.1730
_refine_ls_wR_factor_ref         0.1746
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                8112
_reflns_number_total             8251
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   5.53
_oxford_diffrn_Wilson_scale      0.10
_oxford_refine_ls_scale          3.54(6)
_oxford_structure_analysis_title 7355
_cod_data_source_file            d1sc00856k2.cif
_cod_data_source_block           2j
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               1561134
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0752
_reflns_number_all               8251
_oxford_hooft_y                  0.
_oxford_bijvoet_difference       0.
_oxford_refined_flack_x          0.003(5)