Diastereoselective formal [3 + 3] cycloaddition of isatin-based α-(trifluoromethyl)imines with N,N′-dialkyloxyureas
Zhao, Hong-Wu; Guo, Jia-Ming; Wang, Li-Ru; Ding, Wan-Qiu; Tang, Zhe; Song, Xiu-Qing; Wu, Hui-Hui; Fan, Xiao-Zu; Bi, Xiao-Fan; Organic Chemistry Frontiers 6 (2019) 3891–; doi:10.1039/C9QO01181A

data_1555215
_publ_section_title
;
 Diastereoselective formal [3 + 3] cycloaddition of isatin-based
 \a-(trifluoromethyl)imines with N,N&#x2032;-dialkyloxyureas
;
_journal_issue                   23
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3891
_journal_paper_doi               10.1039/C9QO01181A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C26 H22 Br F3 N4 O4'
_chemical_formula_sum            'C26 H22 Br F3 N4 O4'
_chemical_formula_weight         591.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-26 deposited with the CCDC.	2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.11(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2204(18)
_cell_length_b                   24.665(5)
_cell_length_c                   11.584(2)
_cell_measurement_reflns_used    5868
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      1.6512
_cell_volume                     2543.4(9)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25176
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.888
_diffrn_reflns_theta_min         1.651
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0082(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         6038
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0699P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4597
_reflns_number_total             6038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo01181a2.cif
_cod_data_source_block           shelxl
_cod_database_code               1555215
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.824
_shelx_estimated_absorpt_t_min   0.730
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C25(H25)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              4564
_shelx_hkl_checksum              92197
_olex2_submission_special_instructions 'No special instructions were received'