Methyl (Z)-3-Bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate: Synthesis and Reactions with Dimethyl Malonate and Methyl Acetoacetate
Vasin, V.A.; Bolusheva, I.Yu.; Razin, V.V.; Kapkaeva, S.R.; Petrov, P.S.; Somov, N.V.; Russian Journal of Organic Chemistry 52 (2016) 299–306; doi:10.1134/S1070428016030015

data_4038955
_publ_section_title
;
 Methyl (Z)-3-Bromo-3-(4-methylbenzenesulfonyl)prop-2-enoate: Synthesis
 and Reactions with Dimethyl Malonate and Methyl Acetoacetate
;
_journal_issue                   3
_journal_name_full
;
 Russian Journal of Organic Chemistry
;
_journal_page_first              299
_journal_page_last               306
_journal_paper_doi               10.1134/S1070428016030015
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H11 Br O4 S'
_chemical_formula_weight         319.17
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-25T09:02:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.55980(10)
_cell_length_b                   11.1503(2)
_cell_length_c                   14.9186(3)
_cell_measurement_reflns_used    6620
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.325
_cell_measurement_theta_min      3.892
_cell_volume                     1257.55(4)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0302
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0165653
_diffrn_orient_matrix_UB_12      0.0028478
_diffrn_orient_matrix_UB_13      -0.0467525
_diffrn_orient_matrix_UB_21      0.0917928
_diffrn_orient_matrix_UB_22      -0.0074269
_diffrn_orient_matrix_UB_23      0.0081029
_diffrn_orient_matrix_UB_31      -0.0100813
_diffrn_orient_matrix_UB_32      -0.0631137
_diffrn_orient_matrix_UB_33      -0.0030589
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22493
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         3.531
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.434
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
        (compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.3048
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.587
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0354
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0388P)^2^+0.5663P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_number_gt                2719
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tmp4lmcoo2n
_cod_data_source_block           bp_240615
_cod_database_code               4038955