Catalytic asymmetric formal γ-allylation of deconjugated butenolides.
Simlandy, Amit K.; Mukherjee, Santanu; Organic & biomolecular chemistry 14 (2016) 5659–5664; doi:10.1039/c5ob02362a

data_7154816
_publ_section_title
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 Catalytic asymmetric formal \g-allylation of deconjugated butenolides.
;
_journal_issue                   24
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5659
_journal_page_last               5664
_journal_paper_doi               10.1039/c5ob02362a
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 Br N4 O4 S'
_chemical_formula_sum            'C20 H17 Br N4 O4 S'
_chemical_formula_weight         489.35
_chemical_name_systematic        AKS_I_393_01
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-06-20 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                70.184(2)
_cell_angle_beta                 73.970(2)
_cell_angle_gamma                83.379(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1772(5)
_cell_length_b                   9.7706(5)
_cell_length_c                   13.9947(8)
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.540
_cell_measurement_theta_min      3.088
_cell_volume                     1010.72(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            35218
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  0.6349
_exptl_absorpt_correction_T_min  0.6126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0976 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.8654. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0292P)^2^+0.5610P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0628
_reflns_number_gt                3010
_reflns_number_total             3553
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c5ob02362a3.cif
_cod_data_source_block           3af
_cod_depositor_comments
'Adding full bibliography for 7154815--7154816.cif.'
_cod_database_code               7154816
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C13(H13), C15(H15), C17(H17), C20(H20), C21(H21), C23(H23),
 C25(H25), C27(H27), C30(H30)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_original_sample_id AKS_I_393_01
_olex2_submission_special_instructions 'No special instructions were received'