Lewis Acid-Mediated Ring-Opening Reactions of trans-2-Aroyl-3-styryl-cyclopropane-1,1-dicarboxylates: Access to Cyclopentenes and E,E-1,3-Dienes.
Thangamani, Murugesan; Kannupal, Srinivasan; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02335

data_4033296
_publ_section_title
;
 Lewis Acid-Mediated Ring-Opening Reactions of
 trans-2-Aroyl-3-styryl-cyclopropane-1,1-dicarboxylates: Access to
 Cyclopentenes and E,E-1,3-Dienes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02335
_journal_year                    2017
_chemical_formula_moiety         'C22 H21 Cl O5 S'
_chemical_formula_sum            'C22 H21 Cl O5 S'
_chemical_formula_weight         432.90
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.207(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2076(9)
_cell_length_b                   21.487(2)
_cell_length_c                   11.6395(13)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.01
_cell_measurement_theta_min      2.84
_cell_volume                     2052.7(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.559
_diffrn_measured_fraction_theta_max 0.613
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.559
_diffrn_reflns_Laue_measured_fraction_max 0.613
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11130
_diffrn_reflns_point_group_measured_fraction_full 0.559
_diffrn_reflns_point_group_measured_fraction_max 0.613
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.137
_diffrn_reflns_theta_min         2.657
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             904
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0786
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1584P)^2^+0.3603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2347
_refine_ls_wR_factor_ref         0.2584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2509
_reflns_number_total             3723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02335_si_002.cif
_cod_data_source_block           platon
_cod_database_code               4033296
_shelx_shelxl_version_number     2016/4
_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. Others
 Fixed Sof: C18A(0.8) H18A(0.8) H18B(0.8) C18B(0.2) H18C(0.2) H18D(0.2)
 C19A(0.2) H19D(0.2) H19E(0.2) H19F(0.2) C19B(0.8) H19A(0.8) H19B(0.8) H19C(0.8)
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C18A(H18A,H18B), C18B(H18C,H18D), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16)
3.d Idealised Me refined as rotating group:
 C19A(H19D,H19E,H19F), C19B(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              14139
_shelx_hkl_checksum              24948
_olex2_submission_special_instructions 'No special instructions were received'