Organocatalytic formal [2+2] cycloaddition initiated by vinylogous Friedel-Crafts alkylation: enantioselective synthesis of substituted cyclobutane derivatives
Guo-Jian Duan; Jun-Bing Ling; Wei-Ping Wang; Yong-Chun Luo; Peng-Fei Xu; Chem.Commun. 49 (2013) 4625–; doi:10.1039/c3cc41785a

data_7109276
_publ_section_title
;
 Organocatalytic formal [2+2] cycloaddition initiated by vinylogous
 Friedel-Crafts alkylation: enantioselective synthesis of substituted
 cyclobutane derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              4625
_journal_paper_doi               10.1039/c3cc41785a
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H22 Br N5 O4'
_chemical_formula_sum            'C24 H22 Br N5 O4'
_chemical_formula_weight         524.38
_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
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_atom_sites_solution_secondary   difmap
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Olex2 1.2
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_cell_length_c                   25.1126(10)
_cell_measurement_reflns_used    1060
_cell_measurement_temperature    291.98(10)
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
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_computing_molecular_graphics
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
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O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
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SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
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SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      291.98(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9681
_diffrn_measurement_details
;
1 omega -4.00 24.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- -19.3492 -99.0000 60.0000 28
2 omega 59.00 92.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 57.0000 -150.0000 33
3 omega -19.00 93.00 1.0000 25.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 0.0000 0.0000 112
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
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_diffrn_orient_matrix_UB_21      0.0652826000
_diffrn_orient_matrix_UB_22      0.0317140000
_diffrn_orient_matrix_UB_23      0.0115714000
_diffrn_orient_matrix_UB_31      0.1081413000
_diffrn_orient_matrix_UB_32      -0.0193153000
_diffrn_orient_matrix_UB_33      -0.0067798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
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_diffrn_reflns_av_unetI/netI     0.1134
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_diffrn_reflns_limit_h_min       -6
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_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
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_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         2.92
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.775
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96748
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4294
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1492
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.2118
_reflns_number_gt                2219
_reflns_number_total             4294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41785a.txt
_cod_data_source_block           duangj0916
_cod_original_cell_volume        2369.8(2)
_cod_database_code               7109276
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32