Tandem nucleophilic addition-cycloaddition of arynes with α-iminoesters: two concurrent pathways to imidazolidines.
Jia, Hao; Guo, Zhenyan; Liu, Honglei; Mao, Biming; Shi, Xueyan; Guo, Hongchao; Chemical communications (Cambridge, England) 54 (2018) 7050–7053; doi:10.1039/c8cc03806f

data_7121789
_publ_section_title
;
 Tandem nucleophilic addition-cycloaddition of arynes with \a-iminoesters:
 two concurrent pathways to imidazolidines.
;
_journal_issue                   51
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7050
_journal_page_last               7053
_journal_paper_doi               10.1039/c8cc03806f
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H28 Br2 N2 O4'
_chemical_formula_sum            'C28 H28 Br2 N2 O4'
_chemical_formula_weight         616.34
_chemical_name_common            ' Imidazolidine'
_chemical_name_systematic
'Ethyl (2S,4S,5S)-2,5-bis(4-bromophenyl)-1-(2-ethoxy-2-oxoethyl)-3-phenylimidazolidine-4-carboxylate'
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3572(3)
_cell_length_b                   15.2648(5)
_cell_length_c                   20.6156(6)
_cell_measurement_reflns_used    9427
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.7160
_cell_measurement_theta_min      2.3940
_cell_volume                     2629.95(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            33718
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.917
_diffrn_reflns_theta_min         2.384
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    3.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.357
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.047
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.096
_refine_ls_abs_structure_details
;
 Flack x determined using 1889 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         7669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                5736
_reflns_number_total             7669
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03806f2.cif
_cod_data_source_block           sa5257
_cod_depositor_comments          'Adding full bibliography for 7121789.cif.'
_cod_database_code               7121789
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.402
_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:
 C1(H1), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C15(H15), C16(H16), C18(H18), C19(H19),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              22598
_shelx_hkl_checksum              92944
_olex2_submission_special_instructions 'No special instructions were received'